Organic compound, light emitting diode and light emitting device having the compound

ABSTRACT

The present disclosure relates to an organic compound having a binaphthyl core and a group connected to the biphenyl core and having excellent charge mobility property, and a light emitting diode and a light emitting device having the organic compound. The organic compound can be applied into the light emitting diode by using solution process and has very deep HOMO energy level. When the organic compound is applied into a chare transfer layer, a HOMO energy level bandgap between the charge transfer layer and an emitting material layer is reduced so that holes and electrons can be injected into the emitting material layer in a balanced manner.

CROSS REFERENCE TO RELATED APPLICATION

This application claims the benefit under 35 U.S.C. § 119(a) of KoreanPatent Application No. 10-2018-0159939, filed on Dec. 12, 2018, which ishereby incorporated by reference in its entirety.

BACKGROUND Field of the Disclosure

The present disclosure relates to an organic compound, and morespecifically, to an organic compound that realizes solution process andhas an excellent charge mobility property, and a light emitting diodeand a light emitting device having the same.

Description of the Background

As electronic and information technologies progress, a field of displaysfor processing and displaying a large quantity of information has beendeveloped rapidly. Accordingly, various flat panel display devices suchas a liquid crystal display (LCD) device, an organic light emittingdiode (OLED) display device, etc. have been developed. Among these flatpanel display devices, OLED has come into spotlight as a next-generationdisplay device replacing LCD since it enables thin structure and showslower consumption power.

In case of increasing current densities or raising driving voltages inthe OLED for improving luminance in OLED display device, the luminouslife span of the OLED become shorter owing to thermal degradation anddeteriorations of organic materials in the OLED. Besides, the OLED hasnot achieved high color gamut required in ITU-R Recommendation BT.2020(REC. 2020 or BT.2020) of International Telecommunication Union asregards 4K/UHD standards.

Recently, a display device using inorganic luminescent particles such asquantum dots (QDs) has been developed. QD is an inorganic luminescentparticle that emits light as unstable stated excitons drop fromconduction band to valence band. QD has large extinction coefficient,high quantum yield among inorganic particles and generates strongfluorescence. Besides, since QD has different luminescence wavelengthsas its sizes, it is possible to obtain light within the whole visiblelight spectra so as to implement various colors by adjusting sizes ofQD.

When QD is used as a luminous material in an emitting material layer(EML), it is possible to enhance color purity of individual pixel andimplement white (W) light having high purity of red (R), green (G) andblue (B) so as to achieve Rec.2000 standard. Accordingly, Quantum DotLight emitting Diode (QLED) which uses QD as luminous material has comeinto spotlight.

Surface defects, which is generated at interfaces between emissivelayers or a surface of the emissive layers in the OLED and QLED, hasbeen a limitation in realizing a desired level of luminous efficiency.In addition, since there is a charge un-balancing due to the relativemobility difference between the holes and electrons, the OLED and QLEDshows reduced luminous efficiency.

The OLED or QLED may have multiple laminated films by using solutionprocess. When the material in the lower layer is dissolved in thesolvent used to disperse another material for forming the upper layer,there may occurs mixing of these materials at the interface between theupper and lower layers. Accordingly, when adjacent emissive layers ofthe OLED and QLED are formed through solution process, a compatiblesolvent capable of dispersing and dissolving all the luminous materialsand/or charge transporting material, each of which constitutes theadjacent emissive layers, cannot be used. Therefore, the kinds of thesolvents usable for each emissive layer in the OLED and QLED to whichsolution process is applied are limited. Therefore, there is a need todevelop a material which can be dispersed and dissolved in the limitedsolvent and has an appropriate energy level.

SUMMARY

Accordingly, the present disclosure is directed to an organic compound,a light emitting diode and a light emitting device including the organiccompound that substantially obviates one or more of the problems due tothe limitations and disadvantages of the related art.

More specifically, the present disclosure provides an organic compoundhaving excellent charge mobility rate and can inject charges into anemitting material layer in a balanced manner, and a light emitting diodeand a light emitting device having the organic compound.

In addition, the present disclosure provides an organic compoundrealizing high luminous efficiency and low driving voltage, and a lightemitting diode and a light emitting device having the organic compound.

Additional features and advantages of the disclosure will be set forthin the description which follows, and in part will be apparent from thedescription, or may be learned by practice of the disclosure. Otheradvantages of the disclosure will be realized and attained by thestructure particularly pointed out in the written description and claimshereof as well as the appended drawings.

According to an aspect, the present disclosure provides an organiccompound having the following structure of Chemical Formula 1:

-   -   wherein each of R₁ and R₂ is independently protium, deuterium,        tritium, linear or branched C₁˜C₂₀ alkyl group or C₁˜C₂₀ alkoxy        group; each of a and b is independently an integer of 1 to 3;        each of Ar₁ and Ar₂ is independently C₄˜C₃₀ hetero aryl group or        nitrogen (N), when each of Ar₁ and Ar₂ is independently C₄˜C₃₀        hetero aryl group, each of R₃ and R₄ is independently linear or        branched C₁˜C₁₀ alkyl group, C₅˜C₃₀ aryl amino group        unsubstituted or substituted with linear or branched C₁˜C₁₀        alkyl group, C₄˜C₃₀ hetero aryl amino group unsubstituted or        substituted with linear or branched C₁˜C₁₀ alkyl group, C₅˜C₃₀        aryl group unsubstituted or substituted with a group selected        from the group consisting of linear or branched C₁˜C₁₀ alkyl        group, C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero aryl group and        combination thereof, or C₄˜C₃₀ hetero aryl group unsubstituted        or substituted with a group selected from the group consisting        of linear or branched C₁-C₁₀ alkyl group, C₅˜C₃₀ aryl group,        C₄˜C₃₀ hetero aryl group and combination thereof, and each of c        and d is independently a number of substituents R₃ and R₄ and an        integer of 1 to 3, when each of Ar₁ and Ar₂ is independently        nitrogen (N), each of R₃ and R₄ is independently C₅˜C₃₀ aryl        group unsubstituted or substituted with a group selected from        the group consisting of linear or branched C₁˜C₁₀ alkyl group,        C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero aryl group and combination        thereof, or C₄˜C₃₀ hetero aryl group unsubstituted or        substituted with a group selected from the group consisting of        linear or branched C₁˜C₁₀ alkyl group, C₅˜C₃₀ aryl group, C₄˜C₃₀        hetero aryl group and combination thereof, and each of c and d        is a number of substituents and 2; each of L₁ and L₂ is        independently unsubstituted or substituted C₅˜C₃₀ arylene group        or C₄˜C₃₀ hetero arylene group; and each of m and n is        independently integer of 0 or 1.

According to another aspect, the present disclosure provides a lightemitting diode comprises first and second electrodes facing each otherand an emissive layer between the first and second electrodes andincluding a hole transfer layer, wherein the hole transfer layerincludes the organic compound.

According to still another aspect, the present disclosure provides alight emitting device comprising a substrate and the light emittingdiode as described above.

It is to be understood that both the foregoing general description andthe following detailed description are examples and are explanatory andare intended to provide further explanation of the disclosure asclaimed.

BRIEF DESCRIPTION OF THE DRAWINGS

The accompanying drawings, which are included to provide a furtherunderstanding of the disclosure, are incorporated in and constitute apart of the disclosure, illustrate implementations of the disclosure andtogether with the description serve to explain the principles of aspectsof the disclosure.

In the drawings:

FIG. 1 is a schematic cross-sectional view illustrating a light emittingdisplay device of the present disclosure;

FIG. 2 is a schematic cross-sectional view illustrating a light emittingdiode having a normal structure in accordance with an exemplary aspectof the present disclosure;

FIG. 3 is a schematic diagram illustrating energy levels among materialsin an emissive layers between electrodes in the related art;

FIG. 4 is a schematic diagram illustrating energy levels among materialsin emissive layers between electrodes in accordance with an exemplaryaspect of the present disclosure;

FIG. 5 is a schematic cross-sectional view illustrating a light emittingdiode having a normal structure in accordance with another exemplaryaspect of the present disclosure;

FIG. 6 is a schematic cross-sectional view illustrating a light emittingdiode having an inverted structure in accordance with another exemplaryaspect of the present disclosure;

FIG. 7 is a schematic diagram illustrating energy levels among materialsin emissive layers between electrodes in accordance with anotherexemplary aspect of the present disclosure; and

FIG. 8 is a schematic cross-sectional view illustrating a light emittingdiode having an inverted structure in accordance with still anotherexemplary aspect of the present disclosure.

DETAILED DESCRIPTIONS

Reference will be now be made in detail to aspects of the disclosure,examples of which are illustrated in the accompanying drawings.

Organic Compound

The materials used for charge transporting in the light emitting diodeshould have excellent charge mobility and can inject charges into anemitting material layer in a balance mode, i.e. should have properenergy levels. In addition, if those materials can form thin filmsthrough a solution process rather than a deposition processes, it ispossible to reduce material wastes. An organic compound in accordancewith an aspect of the present disclosure can satisfy those requirementsand may have the following structure of Chemical Formula 1:

-   -   In Chemical Formula 1, each of R₁ and R₂ is independently        protium, deuterium, tritium, linear or branched C₁˜C₂₀ alkyl        group or C₁˜C₂₀ alkoxy group; each of a and b is independently        an integer of 1 to 3. Each of Ar₁ and Ar₂ is independently        C₄˜C₃₀ hetero aryl group or nitrogen (N). When each of Ar₁ and        Ar₂ is independently C₄˜C₃₀ hetero aryl group, each of R₃ and R₄        is independently linear or branched C₁˜C₁₀ alkyl group, C₅˜C₃₀        aryl amino group unsubstituted or substituted with linear or        branched C₁˜C₁₀ alkyl group, C₄˜C₃₀ hetero aryl amino group        unsubstituted or substituted with linear or branched C₁˜C₁₀        alkyl group, C₅˜C₃₀ aryl group unsubstituted or substituted with        a group selected from the group consisting of linear or branched        C₁˜C₁₀ alkyl group, C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero aryl group        and combination thereof, or C₄˜C₃₀ hetero aryl group        unsubstituted or substituted with a group selected from the        group consisting of linear or branched C₁˜C₁₀ alkyl group,        C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero aryl group and combination        thereof, and each of c and d is independently a number of        substituents R₃ and R₄ and an integer of 1 to 3. When each of        Ar₁ and Ar₂ is independently is nitrogen (N), each of R₃ and R₄        is independently C₅˜C₃₀ aryl group unsubstituted or substituted        with a group selected from the group consisting of linear or        branched C₁˜C₁₀ alkyl group, C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero        aryl group and combination thereof, or C₄˜C₃₀ hetero aryl group        unsubstituted or substituted with a group selected from the        group consisting of linear or branched C₁˜C₁₀ alkyl group,        C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero aryl group and combination        thereof, and each of c and d is a number of substituents and 2.        Each of L₁ and L₂ is independently unsubstituted or substituted        C₅˜C₃₀ arylene group or C₄˜C₃₀ hetero arylene group. And each of        m and n is independently integer of 0 or 1.

As used herein, the term “unsubstituted” means that hydrogen atom isbonded, and in this case hydrogen atom includes protium, deuterium andtritium.

A substituent in “substituted” as used herein may include, but are notlimited to, C₁˜C₂₀ alkyl group unsubstituted or substituted withhalogen, cyano group and/or nitro group; C₁˜C₂₀ alkoxy groupunsubstituted or substituted with halogen, cyano group and/or nitrogroup; halogen atom; cyano group; alkyl halide such as CF₃; and hydroxylgroup, carboxyl group, carbonyl group, amino group, C₁˜C₁₀ alkyl aminogroup, C₅˜C₃₀ aryl amino group, C₄˜C₃₀ hetero aryl amino group, nitrogroup, hydrazyl group, sulfonic group, C₁˜C₂₀ alkyl silyl group, C₁˜C₂₀alkoxy silyl group, C₃˜C₃₀ cycloalkyl group, C₅˜C₃₀ aryl silyl group,C₄˜C₃₀ hetero aryl silyl group, C₅˜C₃₀ aryl group and C₄˜C₃₀ hetero arylgroup, each of which is unsubstituted or substituted with halogen, cyanogroup and/or nitro group, respectively.

As used herein, the term “hetero” described in “hetero aromatic ring”,“hetero aromatic group”, “hetero alicyclic ring”, “hetero cyclic alkylgroup”, “hetero aryl group”, “hetero aralkyl group”, “hetero aryloxylgroup”, “hetero aryl amino group”, “hetero arylene group”, “heteroaralkylene group”, “hetero aryloxylene group”, and the likes means thatat least one carbon atoms, for example 1 to 5 carbon atoms, forming sucharomatic or alicyclic rings are substituted with at least one heteroatoms selected from the group consisting of N, O, S and combinationthereof.

In one exemplary aspect, the C₅˜C₃₀ aryl group, each of whichconstitutes respectively R₃ and R₄ or can be substituted respectively toR₃ and R₄, may include, but are not limited to, an unfused or fused arylgroup such as phenyl, biphenyl, terphenyl, tetraphenyl, naphthyl,anthracenyl, indenyl, phenalenyl, phenanthrenyl, azulenyl, pyrenyl,fluorenyl, tetracenyl, indacenyl and spiro fluorenyl, each of which isindependently unsubstituted or substituted with at least one of C₁˜C₁₀alkyl group, C₅˜C₃₀ aryl group and C₄˜C₃₀ hetero aryl group.

For example, when each of R₃ and R₄ is independently C₅˜C₃₀ aryl group,each of R₃ and R₄ may independently include, but are not limited to,phenyl, naphthyl, anthracenyl, indenyl, phenalenyl, phenanthrenyl,azulenyl, pyrenyl, fluorenyl, tetracenyl, indacenyl or spiro fluorenyl,each of which is unsubstituted or substituted with alkyl group and/oraromatic or hetero aromatic group.

In an alternative aspect, when each of Ar₁ and Ar_(e) is independently anitrogen atom (N) or each of R₃ and R₄ is independently a aryl aminogroup, the C₅˜C₃₀ aryl group substituted to the nitrogen atom of theamino group may by an aryl group consisting of 1-3 aromatic rings. Ifthe number of the aromatic ring substituted to the nitrogen atom becomeslarger, an energy bandgap of the organic compound may be excessivelyreduced due to the excessively long conjugated structures in the wholeorganic compound. For example, the C₅˜C₃₀ aryl group, which may besubstituted to the nitrogen atom of the amino group, may include, butare not limited to, phenyl, biphenyl, naphthyl, anthracenyl and/orfluorenyl, each of which is unsubstituted or substituted with alkylgroup or aromatic or hetero aromatic group.

In another exemplary aspect, the C₄˜C₃₀ hetero aryl group, each of whichconstitutes respectively R₃ and R₄ or can be substituted respectively toR₃ and R₄, may include, but are not limited to, an unfused or fusedhetero aryl group such as pyrrolyl, pyridinyl, pyrimidinyl, pyrazinyl,pyridazinyl, triazinyl, tetrazinyl, imidazolyl, pyrazolyl, indolyl,carbazolyl, benzocarbazolyl, dibenzocarbazolyl, indonocarbazolyl,indenocarbazolyl, benzofuronocarbazolyl, benzothienocarbazolyl,quinolinyl, iso-quinolinyl, phthlazinyl, qunixalinyl, cinnolyl,quinazolinyl, benzoquinolinyl, benzoiso-quinolinyl, benzoquianzolinyl,benzoquinoxalinyl, acridinyl, phenanthrolinyl, furanyl, pyranyl,oxazinyl, oxazolyl, oxadiazolyl, triazolyl, dioxinyl, benzofuranyl,dibenzofuranyl, thiopyranyl, thiazinyl, thiopnehyl, benzothiophenyl,dibenzothiophenyl and N-substituted fluorenyl, each of which isindependently unsubstituted or substituted with at least one of C₁˜C₁₀alkyl group, C₅˜C₃₀ aryl group and C₄˜C₃₀ hetero aryl group.

As an example, when each of R₃ and R₄ is independently C₄˜C₃₀ heteroaryl group, each of R₃ and R₄ independently may be, but are not limitedto, a fused hetero aryl group such as indolyl, quinolinyl,iso-quinolinyl, phthalazinyl, quinoxalinyl, cinnolinyl, quinazolinyl,benzoquinolinyl, benzoiso-quinolinyl, benzoquinazolinyl,benzoquinoxalinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl,inodolocarbazolyl, indenocarbazolyl, benzofurocarbazolyl,benzothienocarbazoly, acridiny, phenanthrolinyl, benzofuranyl,dibenzofuranyl, benzothiophenyl and dibenzothiophenyl, each of which isindependently unsubstituted or substituted with at least one of C₁˜C₁₀alkyl group, C₅˜C₃₀ aryl group and C₄˜C₃₀ hetero aryl group.

In an alternative aspect, when each of Ar₁ and Ar_(e) is independently anitrogen atom (N) or each of R₃ and R₄ is independently a hetero arylamino group, the C₄˜C₃₀ hetero aryl group substituted to the nitrogenatom of the amino group may be an aryl group consisting of 1-3 heteroaromatic rings. For example, the C₄˜C₃₀ hetero aryl group, which may besubstituted to the nitrogen atom of the amino group, may include, butare not limited to, pyrrolyl, pyridinyl, pyrimidinyl, pyrazinyl,pyridazinyl, furanyl, thiophenyl, benzofuranyl, benzothiophenyl,dibenzofuranyl, dibenzothiophenyl, carbazolyl, carbolinyl, acridinyl,phenazinly, phenoxazinyl and/or phenothiazinyl, each of which isunsubstituted or substituted with alkyl group or aromatic ring or heteroaromatic group.

In one non-limited aspect, each of L₁ and L₂, a linker in ChemicalFormula 1, mediates the binaphthyl core and each of Ar₁ and Ar_(e),which is a group having excellent hole mobility property, and may be anaromatic or hetero aromatic linker. For example, when each of L₁ and L₂is independently unsubstituted or substituted C₅˜C₃₀ arylene group, eachof L₁ and L₂ may include, but are not limited to, phenylene,biphenylene, terphenylene, tetraphenylene, indenylene, naphthylene,azulenylene, indacenylene, acenaphthylene, fluorenylene,spiro-fluorenylene, phenalenylene, phenanthrenylene, anthracenylene,fluoranthrenylene, triphenylenylne, pyrenylene, chrysenylene,naphthacenylene, picenylene, perylenylene, pentaphenylene andhexacenylene, each of which is unsubstituted or substituted.

In an alternative aspect, when each of L₁ and L₂ is independentlyunsubstituted or substituted C₄˜C₃₀ hetero arylene group, each of L₁ andL₂ may include, but are not limited to, pyrrolylene, imidazolylene,pyrazolylene, pyridinylene, pyrazinylene, pyrimidinylene,pyridazinylene, isoindolylene, indolylene, indazolylene, purinylene,quinolinylene, isoquinolinylene, benzoquinolinylene, phthalazinylene,naphthyridinylene, quinoxalinylene, quinazolinylene, benzoquinolinylene,benzoisoquinolinylene, benzoquinazolinylene, benzoquinoxalinylene,cinnolinylene, phenanthridinylene, acridinylene, phenanthrolinylene,phenazinylene, benzoxazolylene, benzimidazolylene, furanylene,benzofuranylene, thiophenylene, benzothiophenylene, thiazolylene,isothiazolylene, benzothiazolylene, isoxazolylene, oxazolylene,triazolylene, tetrazolylene, oxadiazolylene, triazinylene,dibenzofuranylene, benzofurodibenzofuranylene,benzothienobenzofuranylene, benzothienodibenzofuranylene,dibenzothiophenylene, benzothienobenzothiophenylene,benzothienodibenzothiophenylene, carbazolyene, benzocarbazolylene,dibenzocarbazolylene, indolocarbazolylene, indenocarbazolylene,benzofurocarbazolylene, benzothienocarbazolylene, imidazopyrimidinyleneand imidazopyridinylen, each of which is unsubstituted or substituted.

In an exemplary aspect, when the number of the aromatic or heteroaromatic ring becomes larger, an energy bandgap of the organic compoundmay be excessively reduced due to the excessively long conjugatedstructures in the whole organic compound. As an example, each of L₁ andL₂ may independently include 1-2 aromatic or hetero aromatic rings,alternatively one aromatic or hetero aromatic ring. With regard tocharge injection and/or transportation properties, each of L₁ and L₂ maybe a 5-membered to a 7-membered aromatic or hetero aromatic ring,alternatively a 6-membered aromatic or hetero aromatic ring. Forexample, each of L₁ and L₂ may independently include, but are notlimited to, phenylene, biphenylene, naphthylene, pyrrolylene,imidazoylene, pyridylene, pyrazolylene, pyridinylene, pyrazinylene,pyrimidinylene, pyridazinylene, furanlyene and thiophenylene, each ofwhich is unsubstituted or substituted.

In still another exemplary aspect, R₁ and R₂, Ar₁ and Ar_(e), R₃ and R₄,L₁ and L₂, a to c and/or m and n may be identical to each other.

Since the organic compound having the structure of Chemical Formula 1includes a fused aromatic core including a binaphthyl core, the compoundmay have a deep or low Highest Occupied Molecular Orbital (HOMO) energylevel. When the organic compound having the structure of ChemicalFormula 1 is introduced into a hole transfer layer, it is possible toreduce a HOMO energy level bandgap between the hole transfer layer and aemitting material layer, as described below. Moreover, the organiccompound having the structure of Chemical Formula 1 has an excellenthole mobility property and can be laminated in a light emitting diodeusing a solution process.

Accordingly, holes and electrons can be injected into an emittingmaterial layer in a balanced manner by applying the organic compoundhaving the structure of Chemical Formula 1 to the light emitting diode.When the organic compound having the structure of Chemical Formula 1 isapplied into the light emitting diode, holes and electrons, each ofwhich is injected from an anode and cathode, can be transported into theemitting material layer without quenching so as to form effectiveexciton. Accordingly, luminescence can be realized at a region whereluminous materials exist, not the interface between the emittingmaterial layer and adjacent charge transfer layers. As a result, usingthe organic compound having the structure of Chemical Formula 1 enablesthe light emitting diode to enhance its luminous efficiency and to lowerits driving voltage.

In one exemplary aspect, the organic compound having the structure ofChemical Formula 1 may include an organic compound having the followingstructure of Chemical Formula 2:

-   -   In Chemical Formula 2, each of R₁₁ and R₁₂ is independently        protium, deuterium, tritium, linear or branched C₁˜C₁₀ alkyl        group or C₁˜C₁₀ alkoxy group. Each of Ar₃ and Ar₄ is        independently C₁₀˜C₃₀ fused hetero aryl group. Each of R₁₃ and        R₁₄ is independently linear or branched C₁˜C₁₀ alkyl group,        C₅˜C₃₀ aryl amino group unsubstituted or substituted with linear        or branched C₁˜C₁₀ alkyl group, C₄˜C₃₀ hetero aryl amino group        unsubstituted or substituted with linear or branched C₁˜C₁₀        alkyl group, C₅˜C₃₀ aryl group unsubstituted or substituted with        a group selected from the group consisting of linear or branched        C₁˜C₁₀ alkyl group, C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero aryl group        and combination thereof; or C₄˜C₃₀ hetero aryl group        unsubstituted or substituted with a group selected from the        group consisting of linear or branched C₁-C₁₀ alkyl group,        C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero aryl group and combination        thereof. Each of o and p is independently is a number of        substituents R₁₃ and R₁₄ and an integer of 1 to 2. And each of m        and n is identical as defined in Chemical Formula 1.

As an example, each of Ar₃ and Ar₄ in Chemical Formula 2 mayindependently be, but are not limited to, a fused C₁₀˜C₃₀ hetero arylgroup having at least one nitrogen atom. The fused hetero aryl group ofAr₃ and Ar₄ may include, but are not limited to, carbazolyl, acridinyl,carbolinyl, phenanthrenyl, phenanthrolinyl, phenazinly, phenoxazinyl andphenothiazinyl.

In still another exemplary aspect, R11 and R12, Ar3 and Ar4, R13 andR14, m and n and/or o and p in Chemical Formula 2 may be identical toeach other:

In another exemplary aspect, each of Ar₁ and Ar₂ in Chemical Formula 1may independently be a nitrogen atom substituted with aromatic and/orhetero aromatic groups. Such an organic compound may have the followingstructure of Chemical Formula 3:

-   -   In Chemical Formula 3, each of R₂₁ and R₂₂ is independently        protium, deuterium, tritium, linear or branched C₁˜C₁₀ alkyl        group or C₁˜C₁₀ alkoxy group. Each of R₂₃ to R₂₆ is        independently C₅˜C₃₀ aryl group unsubstituted or substituted        with a group selected from the group consisting of linear or        branched C₁˜C₁₀ alkyl group, C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero        aryl group and combination thereof; or C₄˜C₃₀ hetero aryl group        unsubstituted or substituted with a group selected from the        group consisting of linear or branched C₁˜C₁₀ alkyl group,        C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero aryl group and combination        thereof. Each of m and n is identical as defined in Chemical        Formula 1.

In one exemplary aspect, R21 and R22, R23 to R26 and/′or m and n inChemical Formula 3 may be identical to each other.

Particularly, the organic compound, which is excellent in hole mobilityproperty, has very deep HOMO energy level and is capable of solutionprocess, may include anyone having the following structure of ChemicalFormula 4.

Light Emitting Diode and Light Emitting Device

The organic compound having the structure of anyone in Chemical Formulae1 to 4 has a low HOMO energy level and is excellent in hole mobility,and can be laminated by using a solution process, so that the organiccompound can be applied to a light emitting diode. The light emittingdiode having the organic compound having the structure of anyone inChemical Formulae 1 to 4 may be applied to a light emitting device suchas a light emitting display device and a light emitting illuminationdevice. FIG. 1 is a schematic cross-sectional view illustrating a lightemitting display device of the present disclosure.

As illustrated in FIG. 1, a light emitting display device 100 includes asubstrate 102, a thin film transistor Tr over the substrate 102 and alight emitting diode 200 connected to the thin film transistor Tr. Thethin film transistor Tr includes a semiconductor layer 110, a gateelectrode 130, a source electrode 152 and a drain electrode 154.

The substrate 102 may include, but are not limited to, glass, thinflexible material and/or polymer plastics. For example, the flexiblematerial may be selected from the group, but are not limited to,polyimide (PI), polyethersulfone (PES), polyethylenenaphthalate (PEN),polyethylene terephthalate (PET), polycarbonate (PC) and combinationthereof. The substrate 102, over which the thin film transistor Tr andthe light emitting diode 200 are arranged, forms an array substrate.

A buffer layer 104 may be disposed over the substrate 102, and the thinfilm transistor Tr is disposed over the buffer layer 104. The bufferlayer 104 may be omitted.

A semiconductor layer 110 is disposed over the buffer layer 104. In oneexemplary aspect, the semiconductor layer 110 may include, but are notlimited to, oxide semiconductor materials. In this case, a light-shiedpattern (not shown) may be disposed under the semiconductor layer 110,and the light-shield pattern (not shown) can prevent light from beingincident toward the semiconductor layer 110, and thereby preventing thesemiconductor layer 110 from being deteriorated by the light.Alternatively, the semiconductor layer 110 may include polycrystallinesilicon. In this case, opposite edges of the semiconductor layer 110 maybe doped with impurities.

A gate insulating layer 120 made of insulating material is disposed onthe semiconductor layer 110. The gate insulating layer 120 may include,but are not limited to, an inorganic insulating material such as siliconoxide (SiO_(x)) or silicon nitride (SiN_(x)).

A gate electrode 130 made of a conductive material such as a metal isdisposed over the gate insulating layer 120 so as to correspond to acenter of the semiconductor layer 110. While the gate insulating layer120 is disposed over a whole area of the substrate 102 in FIG. 1, thegate insulating layer 120 may be patterned identically as the gateelectrode 130.

An interlayer insulating layer 140 made of an insulating material isdisposed on the gate electrode 130 with covering over an entire surfaceof the substrate 102. The interlayer insulating layer 140 may include,but are not limited to, an inorganic insulating material such as siliconoxide (SiO_(x)) or silicon nitride (SiN_(x)), or an organic insulatingmaterial such as benzocyclobutene or photo-acryl.

The interlayer insulating layer 140 has first and second semiconductorlayer contact holes 142 and 144 that expose both sides of thesemiconductor layer 110. The first and second semiconductor layercontact holes 142 and 144 are disposed over both sides of the gateelectrode 130 with spacing apart from the gate electrode 130. The firstand second semiconductor layer contact holes 142 and 144 are formedwithin the gate insulating layer 120 in FIG. 1. Alternatively, the firstand second semiconductor layer contact holes 142 and 144 are formed onlywithin the interlayer insulating layer 140 when the gate insulatinglayer 120 is patterned identically as the gate electrode 130.

A source electrode 152 and a drain electrode 154, each of which includesa conductive material such as a metal, are disposed on the interlayerinsulating layer 140. The source electrode 152 and the drain electrode154 are spaced apart from each other with respect to the gate electrode130, and contact both sides of the semiconductor layer 110 through thefirst and second semiconductor layer contact holes 142 and 144,respectively.

The semiconductor layer 110, the gate electrode 130, the sourceelectrode 152 and the drain electrode 154 constitute the thin filmtransistor Tr, which acts as a driving element. The thin film transistorTr in FIG. 1 has a coplanar structure in which the gate electrode 130,the source electrode 152 and the drain electrode 154 are disposed overthe semiconductor layer 110. Alternatively, the thin film transistor Trmay have an inverted staggered structure in which a gate electrode isdisposed under a semiconductor layer and source and drain electrodes aredisposed over the semiconductor layer. In this case, the semiconductorlayer may include, but are not limited to, amorphous silicon.

Although not shown in FIG. 1, a gate line and a data line, which crosseach other to define a pixel region, and a switching element, which isconnected to the gate line and the data line, may be further formed inthe pixel region. The switching element is connected to the thin filmtransistor Tr, which is a driving element. Besides, a power line isspaced apart in parallel from the gate line or the data line, and thethin film transistor Tr may further includes a storage capacitorconfigured to constantly keep a voltage of the gate electrode for oneframe.

In addition, the light emitting display device 100 may include a colorfilter (not shown) for absorbing a light emitted from the organic lightemitting diode 200. For example, the color filter (not shown) may absorba light of specific wavelength such as red (R), green (G) or blue (B).In this case, the light emitting display device 100 can implementfull-color through the color filter (not shown).

For example, when the light emitting display device 100 is abottom-emission type, the color filter (not shown) may be disposed onthe interlayer insulating layer 140 with corresponding to the lightemitting diode 200. Alternatively, when the light emitting displaydevice 100 is a top-emission type, the color filter (not shown) may bedisposed over the light emitting diode 200, that is, a second electrode220.

A passivation layer 160 is disposed on the source and drain electrodes152 and 154 over the whole substrate 102. The passivation layer 160 hasa flat top surface and a drain contact hole 162 that exposes the drainelectrode 154 of the thin film transistor Tr. While the drain contacthole 162 is disposed on the second semiconductor layer contact hole 154,it may be spaced apart from the second semiconductor layer contact hole154.

The light emitting diode 200 includes a first electrode 210 that isdisposed on the passivation layer 160 and connected to the drainelectrode 154 of the thin film transistor Tr. The organic light emittingdiode 200 further includes an emission layer 230 as an emitting unit anda second electrode 220 each of which is disposed sequentially on thefirst electrode 210.

The first electrode 210 is disposed in each pixel region. The firstelectrode 210 may be an anode and include a conductive material havingrelatively high work function value. For example, the first electrode210 may include, but are not limited to, a doped or undoped metal oxidesuch as indium-tin-oxide (ITO), indium-zinc-oxide (IZO), indium-tin-zincoxide (ITZO), indium-copper-oxide (ICO), tin oxide (SnO₂), indium oxide(In₂O₃), cadmium:zinc oxide (Cd:ZnO), fluorine:tin oxide (F:SnO₂),indium:tin oxide (In:SnO₂), gallium:tin oxide (Ga:SnO₂) or aluminum:zincoxide (Al:ZnO; AZO). Optionally, the first electrode 210 may include ametal or nonmetal material such as nickel (Ni), platinum (Pt), gold(Au), silver (Ag), iridium (Ir) or a carbon nanotube (CNT), other thanthe above-described metal oxide.

In one exemplary aspect, when the light emitting display device 100 is atop-emission type, a reflective electrode or a reflective layer (notshown) may be disposed under the first electrode 210. For example, thereflective electrode or the reflective layer (not shown) may comprise,but are not limited to, aluminum-palladium-copper (APC) alloy.

In addition, a bank layer 170 is disposed on the passivation layer 160in order to cover edges of the first electrode 210. The bank layer 170exposes a center of the first electrode 210.

An emission layer 230 as an emitting unit is disposed on the firstelectrode 210. In one exemplary aspect, the emission layer 230 may havea mono-layered structure of an emitting material layer. Alternatively,the emission layer 230 may have a multiple-layered structure of a firstcharge transfer layer 340, 440 540 or 640, an emitting material layer350, 450, 550 or 650 and a second charge transfer layer 360, 460, 560 or660 as illustrated in FIGS. 2, 5, 6 and 8. In one exemplary aspect, theorganic compound having the structure of anyone in Chemical Formulae 1to 4 may be induced into the first charge transfer layer 340 or 440, orthe second charge transfer layer 560 or 660. The configuration andlocations of those layers in the emissive layer 230 will be explained inmore detail below.

The second electrode 220 is disposed over the substrate 102 above whichthe emission layer 230 is disposed. The second electrode 220 may bedisposed over a whole display area, may include a conductive materialhaving a relatively low work function value compared to the firstelectrode 210, and may be a cathode. For example, the second electrode220 may include, but are not limited to, Ca, Ba, Ca/Al, LiF/Ca, LiF/Al,BaF₂/Al, CsF/Al, CaCO₃/Al, BaF₂/Ca/Al, Al, Mg, Au:Mg or Ag:Mg.

In addition, an encapsulation film 180 may be disposed over the secondelectrode 220 in order to prevent outer moisture from penetrating intothe light emitting diode 200. The encapsulation film 180 may have, butare not limited to, a laminated structure of a first inorganicinsulating film 182, an organic insulating film 184 and a secondinorganic insulating film 186.

FIG. 2 is a schematic cross-sectional view illustrating a light emittingdiode having a normal structure in accordance with an exemplary aspectof the present disclosure. As illustrated in FIG. 2, the light emittingdiode (LED) 300 in accordance with the first aspect of the presentdisclosure include a first electrode 310, a second electrode 320 facingthe first electrode 310 and an emission layer 330 disposed between thefirst and second electrodes 310 and 320. The emission layer 330 as anemitting unit includes an emitting material layer (EML) 350 disposedbetween the first and second electrodes 310 and 320, a first chargetransfer layer (CTL1) 340 disposed between the first electrode 310 andthe EML 350 and a second charge transfer layer (CTL2) 360 disposedbetween the EML 350 and the second electrode 320.

The first electrode 310 may be an anode such as a hole injectionelectrode. The first electrode 310 may be located over a substrate (notshown in FIG. 2) that may be a glass or a polymer. As an example, thefirst electrode 310 may include, but are not limited to, a doped orundoped metal oxide such as indium-tin-oxide (ITO), indium-zinc-oxide(IZO), indium-tin-zinc oxide (ITZO), indium-copper-oxide (ICO), tinoxide (SnO₂), indium oxide (In₂O₃), cadmium:zinc oxide (Cd:ZnO),fluorine:tin oxide (F:SnO₂), indium:tin oxide (In:SnO₂), gallium:tinoxide (Ga:SnO₂) or aluminum:zinc oxide (Al:ZnO; AZO). Optionally, thefirst electrode 210 may include a metal or nonmetal material such asnickel (Ni), platinum (Pt), gold (Au), silver (Ag), iridium (Ir) or acarbon nanotube (CNT), other than the above-described metal oxide.

The second electrode 320 may be a cathode such as an electron injectionelectrode. As an example, the second electrode 320 may include, but arenot limited to, Ca, Ba, Ca/Al, LiF/Ca, LiF/Al, BaF₂/Al, CsF/Al,CaCO₃/Al, BaF₂/Ca/Al, Al, Mg, Au:Mg or Ag:Mg. As an example, each of thefirst electrode 310 and the second electrode 320 may have a thicknessof, but are not limited to, about 5 to about 300 nm, and alternativelyabout 10 nm to about 200 nm.

In one exemplary aspect, when the LED 300 is a bottom emission-type LED,the first electrode 310 may include, but are not limited to, atransparent conductive metal oxide such as ITO, IZO, ITZO or AZO, andthe second electrode 320 may include, but are not limited to, Ca, Ba,Ca/Al, LiF/Ca, LiF/Al, BaF₂/Al, Al, Mg, or an Ag:Mg alloy.

The CTL1 340 is disposed between the first electrode 310 and the EML350. In this exemplary aspect, the CTL1 340 may be a hole transfer layerthat provides holes into the EML 350. As an example, the CTL1 340 mayinclude a hole injection layer (HIL) 342 disposed adjacently to thefirst electrode 310 between the first electrode 310 and the EML 350, anda hole transport layer (HTL) 344 disposed adjacently to the EML 350between the first electrode 310 and the EML 350.

The HIL 342 facilitates holes injection from the first electrode 310into the EML 350. As an example, the HIL 342 may include, but are notlimited to, an organic material selected from the group consisting ofpoly(ethylenedioxythiophene):polystyrenesulfonate (PEDOT:PSS);4,4′,4″-tris(diphenylamino)triphenylamines (TDATA) doped withtetrafluoro-tetracyano-quinodimethane (F4-TCNQ); p-doped phthalocyaninesuch as zinc phthalocyanine (ZnPc) doped with F4-TCNQ;N,N′-diphenyl-N,N′-bis(1-naphthyl)-1,1′-biphenyl-4,4″-diamine (α-NPD)doped with F4-TCNQ; hexaazatriphenylene-hexanitrile (HAT-CN); and acombination thereof. As an example, the HIL 342 may include the dopantsuch as F4-TCNQ about 1 to about 30% by weight. The HIL 342 may beomitted in compliance with a structure of the LED 300.

The HTL 344 transports holes from the first electrode 310 into the EML350. The HTL 344 may include an organic compound having the structure ofanyone in Chemical Formulae 1 to 4. When the organic compound having thestructure of anyone in Chemical Formulae 1 to 4 is induced into the HTL344, holes and electrons can be injected into the EML 350 in a balancedmanner.

In FIG. 2, while the CTL1 340 as a hole transfer layer is divided intothe HIL 342 and the HTL 344, the CTL1 340 may have a mono-layeredstructure. For example, the CTL1 340 may include only the HTL 344without the HIL 342 or may include the above-mentioned hole transportingmaterial doped with the hole injection material (e.g. PEDOT:PSS).

The CTL1 340 including the HIL 342 and the HTL 344 may be laminated byany vacuum deposition process such as vacuum vapor deposition andsputtering, or by any solution process such as spin coating, dropcoating, dip coating, spray coating, roll coating, flow coating,casting, screen printing and inkjet printing, or a combination thereof.For example, each of the HIL 342 and the HTL 344 may have a thickness,but are not limited to, between about 10 nm and 200 nm, andalternatively about 10 nm and 100 nm.

The EML 350 may include inorganic luminescent particles or organicluminescent material. As an example, the EML 350 may include inorganicluminescent particles such as quantum dots (QDs) or quantum rods (QRs).QDs or QRs are inorganic luminescent particles that emit light asunstable stated excitons drop from conduction band to valence band.

These inorganic luminescent particles have very large extinctioncoefficient, high quantum yield among inorganic particles and generatesstrong fluorescence. In addition, these inorganic luminescent particlesshows different luminescence wavelengths as its sizes, it is possible toemit lights within the whole visible light spectra so as to implementvarious colors by adjusting sizes of these inorganic luminescentparticles. When these inorganic luminescent particles such as QDs and/orQRs are used as a luminous material in the EML 350, it is possible toenhance color purity in individual pixel region and realize White (W)light consisting of red (R), green (G) and blue (B) lights having highcolor purity.

In one exemplary aspect, QDs or QRs may have a single-layered structure.In another exemplary aspect, QDs or QRs may have a multiple-layeredheterologous structure, i.e. core/shell structure. In this case, each ofthe core and the shell may have single layer or multiple layers,respectively. The reactivity of precursors, which can be synthesized tothe core and/or the shell, injection rates of the precursors into areaction vessel, reaction temperature and kinds of ligands bonded to anouter surface of those inorganic luminescent particles such as QDs orQRs may have affect upon the growth rates and crystal structures ofthose inorganic luminescent particles. As a result, it is possible toemit lights of various luminescent wavelength ranges, as the energylevel bandgap of those inorganic luminescent particles are adjusted.

In one exemplary aspect, inorganic luminescent particles (e.g. QDsand/or QRs) may have a type I core/shell structure where an energy levelbandgap of the core is within an energy level bandgap of the shell. Incase of using the type I core/shell structure, electrons and holes aretransferred to the core and recombined in the core. Since the core emitslight from exciton energies, it is possible to adjust luminancewavelengths by adjusting sizes of the core.

In another exemplary aspect, the inorganic luminescent particles (e.g.QDs and/or QRs) may have a type II core/shell structure where the energylevel bandgap of the core and the shell are staggered and electrons andholes are transferred to opposite directions among the core and theshell. In case of using the type II core/shell structure, it is possibleto adjust luminescence wavelengths as the thickness and the energybandgap locations of the shell.

In still another exemplary aspect, the inorganic luminescent particles(e.g. QDs and/or QRs) may have a reverse type I core/shell structurewhere the energy level bandgap of the core is wider than the energylevel bandgap of the shell. In case of using the reverse type Icore/shell structure, it is possible to adjust luminescence wavelengthsas thickness of the shell.

As an example, when the inorganic luminescent particle (e.g. QDs and/orQRs) has a type-I core/shell structure, the core is a region whereluminescence substantially occurs, and a luminescence wavelength of theinorganic luminescent particle is determined as the sizes of the core.To achieve a quantum confinement effect, the core necessarily has asmaller size than the exciton Bohr radius according to material of theinorganic luminescent particle, and an optical bandgap at acorresponding size.

The shell of the inorganic luminescent particles (e.g. QDs and/or QRs)promotes the quantum confinement effect of the core, and determines thestability of the particles. Atoms exposed on a surface of colloidalinorganic luminescent particles (e.g. QDs and/or QRs) having only asingle structure have lone pair electrons which do not participate in achemical bond, unlike the internal atoms. Since energy levels of thesesurface atoms are between the conduction band edge and the valence bandedge of the inorganic luminescent particles (e.g. QDs and/or QRs), thecharges may be trapped on the surface of the inorganic luminescenceparticles (e.g. QDs and/or QRs), and thereby resulting in surfacedefects. Due to a non-radiative recombination process of excitons causedby the surface defects, the luminous efficiency of the inorganicluminescence particles may be degraded, and the trapped charges mayreact with external oxygen and compounds, leading to a change in thechemical composition of the inorganic luminescence particles, or to apermanent loss of the electrical/optical properties of the inorganicluminescent particles.

To effectively form the shell on the surface of the core, a latticeconstant of the material in the shell needs to be similar to that of thematerial in the core. As the surface of the core is enclosed by theshell, the oxidation of the core may be prevented, the chemicalstability of the inorganic luminescence particles (e.g. QDs and/or QRs)may be enhanced, and the photo-degradation of the core by an externalfactor such as water or oxygen may be prevented. In addition, the lossof excitons caused by the surface trap on the surface of the core may beminimized, and the energy loss caused by molecular vibration may beprevented, thereby enhancing the quantum efficiency.

In one exemplary aspect, each of the core and the shell may include, butare not limited to, a semiconductor nanocrystals and/or metal oxidenanocrystals having quantum confinement effect. For example, thesemiconductor nanocrystals of the core and the shell may be selectedfrom the group, but are not limited to, consisting of Group II-VIcompound semiconductor nanocrystals, Group III-V compound semiconductornanocrystals, Group IV-VI compound semiconductor nanocrystals, GroupI-III-VI compound semiconductor nanocrystals and combination thereof.

Particularly, Group II-VI compound semiconductor nanocrystals of thecore and/or the shell may be selected from the group, but are notlimited to, consisting of MgS, MgSe, MgTe, CaS, CaSe, CaTe, SrS, SrSe,SrTe, BaS, BaSe, BaTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeSe, ZnO, CdS, CdSe,CdTe, CdSeS, CdZnS, CdSeTe, CdO, HgS, HgSe, HgTe, CdZnTe, HgCdTe,HgZnSe, HgZnTe, CdS/ZnS, CdS/ZnSe, CdSe/ZnS, CdSe/ZnSe, ZnSe/ZnS,ZnS/CdSZnS, CdS/CdZnS/ZnS, ZnS/ZnSe/CdSe and combination thereof.

Group III-V compound semiconductor nanocrystals of the core and/or shellmay be selected from the group, but are not limited to, consisting ofAN, AlP, AlAs, AlSb, GaN, GaP, Ga₂O₃, GaAs, GaSb, InN, In₂O₃, InP, InAs,InSb, AlGaAs, InGaAs, InGaP, AlInAs, AlInSb, GaAsN, GaAsP, GaAsSb,AlGaN, AlGaP, InGaN, InAsSb, InGaSb, AlGaInP, AlGaAsP, InGaAsP,InGaAsSb, InAsSbP, AlInAsP, AlGaAsN, InGaAsN, InAlAsN, GaAsSbN,GaInNAsSb and combination thereof.

Group IV-VI compound semiconductor nanocrystals of the core and/or shellmay be selected from the group, but are not limited to, consisting ofTiO₂, SnO₂, SnS, SnS₂, SnTe, PbO, PbO₂, PbS, PbSe, PbTe, PbSnTe andcombination thereof. Also, Group I-III-VI compound semiconductornanocrystals of the core and/or shell may be selected from the group,but are not limited to, AgGaS₂, AgGaSe₂, AgGaTe₂, AgInS₂, CuInS₂,CuInSe₂, Cu₂SnS₃, CuGaS₂, CuGaSe₂ and combination thereof.Alternatively, each of the core and the shell may independently includemultiple layers each of which has different Groups compoundsemiconductor nanocrystals, e.g., Group II-VI compound semiconductornanocrystals and Group III-V compound semiconductor nanocrystals such asInP/ZnS, InP/ZnSe, GaP/ZnS, and the likes, respectively.

In another aspect, the metal oxide nanocrystals of the core and/or shellmay include, but are not limited to, Group II or Group III metal oxidenanocrystals. As an example, the metal oxide nanocrystals of the coreand/or the shell may be selected from the group, but are not limited to,MgO, CaO, SrO, BaO, Al₂O₃ and combination thereof.

The semiconductor nanocrystals of the core and/or the shell may be dopedwith a rare earth element such as Eu, Er, Tb, Tm, Dy or an arbitrarycombination thereof or may be doped with a transition metal element suchas Mn, Cu, Ag, Al or an arbitrary combination thereof.

As an example, the core in QDs or QRs may include, but are not limitedto, ZnSe, ZnTe, CdSe, CdTe, InP, ZnCdS, Cu_(x)In_(1-x)S,Cu_(x)In_(1-x)Se, Ag_(x)In_(1-x)S and combination thereof. The shell inQDs or QRs may include, but are not limited to, ZnS, GaP, CdS, ZnSe,CdS/ZnS, ZnSe/ZnS, ZnS/ZnSe/CdSe, GaP/ZnS, CdS/CdZnS/ZnS, ZnS/CdSZnS,Cd_(x)Zn_(1-x)S and combination thereof.

In another exemplary aspect, the inorganic luminescent particle mayinclude, but are not limited to, alloy QD or alloy QR such as homogenousalloy QD or QR or gradient alloy QD or QR, e.g. CdS_(x)Se_(1-x),CdSe_(x)Te_(1-x), Cd_(x)Zn_(1-x)S, Zn_(x)Cd_(1-x)Se, Cu_(x)In_(1-x)S,Cu_(x)In_(1-x)Se, Ag—In_(1-x)S.

When the EML 350 includes inorganic luminescent particles such as QDsand/or QRs, the EML 350 may be laminated through any solution process,i.e. coating the dispersion solution, which contains inorganicluminescent particles dissolved in a solvent, on the CTL1 340, forexample the HTL 344, and evaporating the solvent. In one aspect, the EML350 may be laminated on the CTL1 340 using any solution process such asspin coating, drop coating, dip coating, spray coating, roll coating,flow coating, casting, screen printing and inkjet printing, or acombination thereof.

In one exemplary aspect, the EML 350 may include inorganic luminescentparticles such as QDs and/or QRs having photoluminescence (PL)wavelength peaks of 440 nm, 530 nm, and 620 nm so as to realize whiteLED. Optionally, the EML 350 may include inorganic luminescent particlessuch as QDs or QRs having any one of red, green and blue colors, and maybe formed to emit any one color.

In an alternative aspect, the EML 350 may include an organic luminousmaterial. The organic luminous material is not limited to specificorganic luminous material. As an example, the EML 350 may include anorganic luminous material that emits red (R), green (G) or blue (B)light, and may include fluorescent material or phosphorescent material.As an example, the organic luminous material in the EML 350 may includea host and a dopant. When the organic luminous material constitutes ahost-dopant system, the EML 350 may include the dopant, but are notlimited to, about 1 to about 50% by weight, and alternatively about 1 toabout 30% by weight.

The organic host, which can be used in the EML 350, is not limited tospecific organic luminous material. As an example, the organic host inthe EML 350 may include, but are not limited to,Tris(8-hydroxyquinoline)aluminum (Alq₃), TCTA, PVK,4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP),4,4′-Bis(9-carbazolyl)-2,2′-dimethylbiphenyl (CDBP),(9,10-di(naphthalene-2-yl)anthracene (ADN),3-tert-butyl-9,10-di(naphtha-2-yl)anthracene (TB ADN),2-methyl-9,10-bis(naphthalene-2-yl) anthracene (MADN),1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBi), distyrylarylene(DSA), mCP and/or 1,3,5-tris(carbazol-9-yl)benzene (TCP).

In one exemplary aspect, when the EML 350 emits red light, the dopant inthe EML 350 may include, but are not limited to, an organic compoundand/or a metal complex such as 5,6,11,12-tetraphenylnaphthalene(Rubrene),(Bis(2-benzo-thiophene-2-yl-pyridine)(acetylacetonate)iridium(III)(Ir(btp)₂(acac)),Bis[1-(9,9-dimethyl-9H-fluorn-2-yl)-isoquinoline](acetylacetonate)iridium(III)(Ir(fliq)₂(acac)),Bis[2-(9,9-dimethyl-9H-fluorn-2-yl)-quinoline](acetylacetonate)iridium(III)(Ir(flq)₂(acac)),Bis-(2-phenylquinoline)(2-(3-methylphenyl)pyridinate)irideium(III)(Ir(phq)₂typ) and/orIridium(III)bis(2-(2,4-difluorophenyl)quinoline)picolinate (FPQIrpic).

In another exemplary aspect, when the EML 350 emits green light, thedopant in the EML 350 may include, but are not limited to, an organiccompound and/or a metal complex such as N,N′-dimethyl-quinacridone(DMQA), coumarine 6,9,10-bis[N,N-di-(p-tolyl)amino]anthracene (TTPA),9,10-bis[phenyl(m-tolyl)-amino]anthracene (TPA),bis(2-phenylpyridine)(acetylacetonate)iridium(III) (Ir(ppy)₂(acac)),fac-tris(phenylpyridine)iridium(III) (fac-Ir(ppy)₃) and/ortris[2-(p-tolyl)pyridine]iridium(III) (Ir(mppy)₃).

In still another exemplary aspect, when the EML 350 emits blue right,the dopant in the EML 350 may include, but are not limited to, anorganic compound and/or a metal complex such as4,4′-bis[4-(di-p-tolylamino)styryl]biphenyl (DPAVBi), perylene,2,5,8,11-tetra-tert-butylpherylene (TBPe),bis(3,5-difluoro-2-(2-pyridyl)phenyl-(2-carbozylpyridyl)iridium(III)(FirPic), mer-tris(1-phenyl-3-methylimidazolin-2ylidene-C,C2′)iridium(DI (mer-Ir(pmi)₃) and/ortris(2-(4,6-difluorophenyl)pyridine)iridium(III) (Ir(Fppy)₃).

Alternatively, when the EML 350 includes an organic luminous material,the EML 350 may include a delayed fluorescent material.

When the EML 350 includes an organic luminous material, the EML 350 maybe laminated by any vacuum deposition process such as vacuum vapordeposition and sputtering, or by any solution process such as spincoating, drop coating, dip coating, spray coating, roll coating, flowcoating, casting, screen printing and inkjet printing, or a combinationthereof.

For example, the EML 350 may have a thickness, but are not limited to,between about 5 nm and about 300 nm, and alternatively about 10 nm andabout 200 nm.

In accordance with an exemplary aspect, the EML 350 may includeinorganic luminescent particles such as QDs and/or QRs. Even if the LED300 has high luminance by increasing current density or driving voltage,the inorganic luminescent particles are not degraded, so that the lifespan of the LED 300 may not be reduced.

The CTL2 360 is disposed between the EML 350 and the second electrode320. The CTL2 360 may be an electron transfer layer which provideselectrons into the EML 350. In one exemplary aspect, the CTL2 360 mayinclude an electron injection layer (EIL) 362 disposed adjacently to thesecond electrode 320 between the second electrode 320 and the EML 350,and an electron transport layer (ETL) 364 disposed adjacently to the EML350 between the second electrode 320 and the EML 350.

The EIL 362 facilitates the injection of electrons from the secondelectrode 320 into the EML 350. For example, the EIL 362 may include,but are not limited to, a metal such as Al, Cd, Cs, Cu, Ga, Ge, Inand/or Li, each of which is undoped or doped with fluorine; and/or metaloxide such as titanium dioxide (TiO₂), zinc oxide (ZnO), zirconium oxide(ZrO), tin oxide (SnO₂), tungsten oxide (WO₃) and/or tantalum oxide(Ta₂O₃), each of which is undoped or doped with Al, Mg, In, Li, Ga, Cd,Cs or Cu.

The ETL 364 transfers electrons into the EML 350. The ETL 364 mayinclude inorganic and/or organic materials. In one exemplary aspect,when the EML 350 includes inorganic luminescent particles, the ETL 364may include an inorganic material so as to prevent an interface defectfrom being formed at an interface between the EML 350 and the ETL 364,and thereby securing driving stability of the LED 300. When the ETL 364includes an inorganic material having high charge mobility, the electrontransport rate provided from the second electrode 320 may be improved,and electrons can be transported efficiently into the EML 350 owing tohigh electron levels or concentrations.

In addition, when the EML 350 includes an inorganic luminescentparticle, the inorganic luminescent particle in the EML 350 typicallyhas a very deep valence band (VB) energy level, which corresponds to ahighest occupied molecular orbital (HOMO) energy level of an organicmaterial, compared to a HOMO energy level of an organic luminousmaterial. An organic compound having electron transporting propertytypically has a shallower HOMO energy level than the VB energy level ofthe inorganic luminescent particle. In this case, the holes, injectedfrom the first electrode 310 into the EML 350 having the inorganicluminescent particles, may be leaked toward the second electrode via theETL 364 including the organic compound as an electron transportingmaterial.

In one exemplary aspect, the ETL 364 may include an inorganic materialhaving relatively deep VB energy level compared to VB energy level orHOMO energy level of the luminous material in the EML 350. As anexample, an inorganic material having wide energy level bandgap (Eg)between the VB energy level and a conduction band energy level, whichcorresponds to a lowest unoccupied molecular orbital (LUMO) energy levelof an organic compound, may be used as an electron transporting materialof the ETL 364. In this case, the holes, injected from the firstelectrode 310 into the EML 350 having the inorganic luminescentparticles, cannot be leaked to the ETL 364, and electrons provided fromthe second electrode 320 can be injected efficiently into the EML 350.

As an example, when the ETL 364 includes an inorganic material, the ETL364 may include, but are not limited to, a metal oxide undoped or dopedwith at least one of Al, Mg, In, Li, Ga, Cd, Cs and Cu; a semiconductorparticle undoped or doped with at least one of Al, Mg, In, Li, Ga, Cd,Cs and Cu; metal nitrides; and combination thereof.

In one exemplary aspect, the metal component of the metal oxide in theETL 364 may be selected from, but are not limited to, zinc (Zn), calcium(Ca), magnesium (Mg), titanium (Ti), tin (Sn), tungsten (W), tantalum(Ta), hafnium (Hf), aluminum (Al), zirconium (Zr), barium (Ba) andcombination thereof. Particularly, the metal oxide in the ETL 364 mayinclude, but are not limited to, titanium dioxide (TiO₂), zinc oxide(ZnO), magnesium zinc oxide (ZnMgO), zirconium oxide (ZrO), tin oxide(SnO₂), tungsten oxide (WO₃), tantalum oxide (Ta₂O₃), hafnium oxide(HfO₃), aluminum oxide (Al₂O₃), barium titanium oxide (BaTiO₃), andbarium zirconium oxide (BaZrO₃), each of which is undoped or doped withAl, Mg, In, Li, Ga, Cd, Cs or Cu.

Other inorganic material in the ETL 364 may include, but are not limitedto, a semiconductor particle such as CdS, ZnSe, ZnS, each of which isundoped or doped with Al, Mg, In, Li, Ga, Cd, Cs or Cu; nitrides such asSi₃N₄; and combination thereof.

In another exemplary aspect, when the ETL 364 includes an organicmaterial, the ETL 364 may include, but are not limited to, oxazole-basedcompounds, isooxazole-based compounds, triazole-based compounds,isotriazole-based compounds, oxadiazole-based compounds,thiadiazole-based compounds, phenanthroline-based compounds,perylene-based compound, benzoxazole-based compounds,benzothiazole-based compounds, benzimidazole-based compounds,triazine-based compounds and/or aluminum complexes. Particularly, theorganic material of the ETL 364 may include, but are not limited to,3-(biphenyl-4-yl)-5-(4-tertbutylphenyl)-4-phenyl-4H-1,2,4-triazole(TAZ), bathocuproine (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline;BCP), 2,2′,2″-(1,3,5-Benzinetriyl)-tris(1-phenyl-1-H-benzimidazole)(TPBi), Tris(8-hydroxyquinoline)aluminum (Alq₃),Bis(2-methyl-8-quninolinato)-4-phenylphenolatealuminum(III) (Balq),bis(2-methyl-quinolinato)(tripnehylsiloxy) aluminum(III) (Salq) andcombination thereof.

Similar to the CTL1 340, while FIG. 2 illustrates the CTL2 360 as abi-layered structure including the EIL 362 and the ETL 364, the CTL2 360may have a mono-layered structure having only the ETL 364.Alternatively, the CTL2 360 may have a mono-layered structure of ETL 364including a blend of the above-described electron-transporting inorganicmaterial with cesium carbonate.

The CTL2 360, which includes the EIL 362 and/or the ETL 364, may belaminated on the EML 350 by any vacuum deposition process such as vacuumvapor deposition and sputtering, or by any solution process such as spincoating, drop coating, dip coating, spray coating, roll coating, flowcoating, casting, screen printing and inkjet printing, or combinationthereof. As an example, each of the EIL 362 and the ETL 364 may have athickness, but are not limited to, between about 10 nm and about 200 nm,and alternatively about 10 nm and 100 nm.

For example, the LED 300 may have a hybrid charge transfer layer (CTL)in which the HTL 344 of the CTL1 340 includes the organic material asdescribe above and the CTL2 360, for example, the ETL 364 includes theinorganic material as described above. In this case, The LED 300 mayenhance its luminous properties.

When holes are transported to the second electrode 320 through the EML350, or electrons are transported to the first electrode 310 through theEML 350, the lifespan and efficiency of the LED 300 may be reduced. Toprevent such deterioration, the LED 300 may further include at least oneexciton blocking layer disposed adjacently to the EML 350.

For example, the LED 300 may include an electron blocking layer (EBL)capable of controlling and preventing the transfer of electrons betweenthe HTL 344 and the EML 350. As an example, the EBL (not shown) mayinclude, but are not limited to, TCTA,tris[4-diethylamino)phenyl]amine),N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine,tri-p-tolylamine, 1,1-bis(4-(N,N′-di(ptolyl)amino)phenyl)cyclohexane(TAPC), m-MTDATA, 1,3-bis(N-carbazolyl)benzene (mCP),3,3′-bis(N-carbazolyl)-1,1′-biphenyl (mCBP), Poly-TPD, copperphthalocyanine (CuPc), DNTPD and/or1,3,5-tris[4-diphenylamino)phenyl]benzene (TDAPB), and combinationthereof.

In addition, a hole blocking layer (HBL), as a second exciton blockinglayer, may be disposed between the EML 350 and the ETL 364 to preventthe transfer of holes between the EML 350 and the ETL 364. In oneexemplary aspect, the HBL (not shown) may include, but are not limitedto, oxadiazole-based compounds, triazole-based compounds,phenanthroline-based compounds, benzoxazole-based compounds,benzothiazole-based compounds, benzimidazole-based compounds,triazine-based compounds, and the likes, which may be used for the ETL364. For example, the HBL (not shown) may include, but are not limitedto, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), BAlq, Alq3,PBD, spiro-PBD and/or Liq, which have/has a deeper HOMO energy levelthan that of the material used for the EML 350.

As described above, the organic compound having the structure of anyonein Chemical Formulae 1 to 4 includes a fused aromatic ring having abinaphthyl core so that the organic compound shows a very deep or lowHOMO energy level. In addition, since the organic compound includes atleast one substituent having an excellent hole mobility property, theorganic compound has enhanced hole transporting property. Accordingly,holes and electrons can be injected into the EML 350 in a balancedmanner in the LED 300 including the organic compound.

FIG. 3 is a schematic diagram illustrating energy levels among materialsin an emissive layers between electrodes in the prior art. A lightemitting diode is a device that emits light as charge carriers areinjected into an EML, which includes a luminous material, between a holeinjection electrode (first electrode) and an electron injectionelectrode (second electrode), and then those charge carriers such aselectrons “

” and holes “

⁺” form excitons and then disappear. The holes “

⁺” injected from the first electrode and the electrons “

” injected from the second electrode are recombined with each other inthe EML to from excitons. The energy, which is generated in the courseof forming excitons, enables the luminous material in the EML to beexcited state and can be emitted light energy form.

Both the HIL 342 and the HTL 344 inject and transport positive chargecarriers, i.e. holes “

⁺” into the EML from the first electrode 310, and the ETL injects andtransports negative charge carriers, i.e. electrons “

” into the EML 350 from the second electrode 320. Each layer in theemissive layer 330 must include material having appropriate energy leveland energy level bandgap so as to inject or transport the holes “

⁺” and electrons “

” into the EML 350.

The luminous material of the EML has a lower or deeper HOMO energy levelHOMO_(EML) than a HOMO energy level HOMO_(HTL) of the prior-art holetransporting material of the HTL. Particularly, when the EML 350includes an inorganic luminescent particles such as QDs or QRs as aluminous material, the VB energy level VB_(EML) of these inorganicluminescent particles, which corresponds to a HOMO energy level of theorganic compounds, is much lower than a HOMO energy level of an organicluminous material.

In addition, the luminous material in the EML 350 has a high conductionband energy level CV_(EML) (inorganic material) or Lowest UnoccupiedMolecular Orbital (LUMO) energy level LUMO_(EML). Accordingly, when theholes are transported from the HTL to the EML as well as when theelectrons are transported from the ETL to the EML, energy barriers areformed between the EML and the HTL or ETL owing to energy level bandgapbetween the luminous material in the EML 350 and charge transportingmaterials in the charge transport layers HTL 344 and ETL 364 disposedadjacently to the EML 350.

However, the energy level bandgap “ΔG_(H)” between the HOMO energy levelHOMO_(HTL) of the HTL 344 and the HOMO energy level HOMOEML of the EML350 is much larger than the energy level bandgap “ΔG_(L)” between theLUMO energy level LUMO_(ETL) of the ETL 364 and the LUMO energy levelLUMO_(EML) of the EML 350. In other words, the luminous material of theEML 350 has a very lower HOMO energy level HOMO_(EML) compared to theHOMO energy level HOMO_(HTL) of the prior-art hole transportingmaterials in the HTL.

Accordingly, the holes transportations and injections into the EML aredelayed compared to the electrons transportations injections into theEML, i.e., the holes “

⁺” are injected slowly than the electrons “

” into the EML. As a result, positive charged carriers, holes ““

⁺” and negative charged carriers, electrons “

” cannot be injected into the EML in a balanced manner. Particularly,when the EML includes an inorganic luminescent material having very lowvalence band energy level VB_(EML), the injection unbalance betweenholes “

⁺⁺” and electrons “

” into the EML becomes more serious.

As excessive amount of electrons “

” are injected compared to an amount of holes “

⁺”, a large amount of the excessively injected electrons “

” does not recombine with the holes “

⁺” and thus is quenched without forming excitons (electron quenching).As electrons “

” are injected into the EML excessively compared to holes

⁺”, electrons “

” and holes “

⁺” are recombined at an interface between the EML and the HTL, not inthe luminous materials within the EML. Due to the charge unbalancing,not only the luminous efficiency of the LED is lowered but also a highdriving voltage is required in order to realize a desired luminescence,which results in increase in power consumption.

On the contrary, since the HTL 344 includes an organic compound havingthe structure anyone in Chemical Formulae 1 to 4, it is possible tosolve those charge unbalancing. FIG. 4 is a schematic diagramillustrating energy levels among materials in emissive layers betweenelectrodes in accordance with an exemplary aspect of the presentdisclosure.

As illustrated in FIG. 4, when the organic compound having the structureof anyone in Chemical Formulae 1 to 4 is used in the CTL1, for example,HTL 344, the whole HOMO energy level HOMO_(HTL) of the HTL 344 becomeslower (deep HOMO_(HTL)). As the energy level energy bandgap “ΔG′_(H)”between the HOMO energy level HOMO_(HTL) of the HTL 344 and the HOMOenergy level HOMO_(EML) of the EML 350 is reduced, i.e.“Δ′G_(H)”<“ΔG_(H)”, the energy barrier between the HTL 344 and the EML350 may be removed. In other words, when the organic compound has thestructure of anyone in Chemical Formulae 1 to 4, the energy levelbandgap “Δ′G_(H)” between the HOMO energy level HOMO_(HTL) of the HTL344 and the HOMO energy level HOMO_(EML) of the EML 350 is substantiallythe same as the energy level bandgap “ΔG_(L)” between the LUMO energylevel LUMO_(ETL) or conduction band energy level CB_(ETL) of the ETL 364and the LUMO energy level LUMO_(EML) of the EML 350.

When the organic compound having the structure of anyone in ChemicalFormulae 1 to 4 is used as a material in the HTL 344, since theelectrons “

” and the holes “

⁺” can be injected into the EML in a balanced manner to form excitons,the amount of electrons that is quenched without forming excitons can bereduced or minimized. Since the electrons “

” and holes “

⁺” are recombined with each other in the luminous material within theEML 350, not at interfaces between the EML 350 and adjacent CTL (e.g.HTL or ETL), and thereby resulting in efficient light emissions.Accordingly, the LED 300 can maximize its luminous efficiency and lowerpower consumption since it can be driven at lower voltage.

In one exemplary aspect, the HTL 344 includes only the organic compoundhaving the structure of anyone in Chemical Formulae 1 to 4. In anotherexemplary aspect, the organic compound having the structure of anyone inChemical Formulae 1 to 4 may be used as a dopant in the HTL 344. In thiscase, the HTL 344 may include a host. The host may include, but are notlimited to, an organic material having an aryl amine moiety, a fluorenemoiety and/or an carbazole moiety, each of which has excellent holemobility. As an example, the host of the HTL 344 may include, but arenot limited to, any organic material having each of the followingstructure of Chemical Formulae 5 to 8:

-   -   In Chemical Formulae 5 to 7, each of R₃₁ to R₃₄ is independently        unsubstituted or substituted linear or branched C₁˜C₂₀ alkyl        group, unsubstituted or substituted C₁˜C₂₀ alkoxy group,        unsubstituted or substituted C₅˜C₃₀ aryl group or unsubstituted        or substituted C₄˜C₃₀ hetero aryl group. Each of a and b is        independently an integer of 1 to 4. In Chemical Formula 8, m is        an integer of 1 to 10. In Chemical Formulae 5 to 8, n is an        integer of equal to or more than 1.

When the HTL 344 includes the host and the dopant, the HTL 344 mayinclude the organic compound having the structure of anyone in ChemicalFormulae 1 to 4 of about 1 to about 50% by weight, but are not limitedthereto.

In one exemplary aspect, each of R₃₁ to R₃₄ in Chemical Formulae 5 to 7may be independently unsubstituted or substituted linear or branchedC₁˜C₁₀ alkyl group. As an example, the organic material having thestructure of anyone in Chemical Formulae 5 to 8 may include, but are notlimited to, Poly[N,N′-bis(4-butylphenyl)-N,N′-bis(phenyl)-benzidine](poly-TPD, p-TPD),poly[(9,9-dioctylflorenyl-2,7-diyl)-co-(4,4′-(N-(4-sec-butylphenyl)diphenylamine))](TFB), poly(N-vinylcarbazole (PVK),poly[bis(4-phenyl)(2,4,6-trimethylphenyl)amine] (PTAA) and the likes.

In an alternative aspect, the host in the HTL 344 may include an organicmaterial having a non-polymer structure. The hole transporting hosthaving the non-polymer structure may include, but are not limited to,N,N′-Bis(3-methylphenyl)-N,N′-bis(phenyl)benzidine (TPD),N,N′-Bis(3-methylphenyl)-N,N′-bis(phenyl)-2,7-diamino-9,9′-spirofluorene(spiro-TPD),N,N′-Bis(3-methylphenyl)-N,N′-bis(phenyl)-9,9′-dioctylfluorene(DOFL-TPD),N²,N⁷-Di(naphthalene-1-yl)-9,9-dioctyl-N2,N7-diphenyl-9H-fluorene-2,7-diamine(DOFL-NPB), N,N′-Bis(4-methylphenyl)-N,N′-bis(phenyl)benzidine),N¹,N⁴-diphenyl-N¹,N⁴-di-m-tolylbenzene-1,4-diamine (TTP),N,N,N′,N′-tetra(3-methylphenyl)3,3′-dimethylbenzidien (HMTPD),di-[4-(N,N′-di-p-tolyl-amino)-phenyl]cyclohexane (TAPC),N⁴,N⁴′-Bis(4-(6-((3-ethyloxetan-3-yl)methoxy)hexyl)phenyl)-N4,N4′-diphenylbiphenyl-4,4′-diamine(OTPD), 4,4′,4″-tris(N,N-phenyl-3-methylphenylamino)triphenylamine), andthe likes.

In one exemplary aspect, the HLT 344 may include the organic materialhaving the polymer structure of anyone in Chemical Formulae 5 to 8 as ahost and the organic compound having the structure of anyone in ChemicalFormulae 1 to 4 as a dopant. In this case, the hole mobility property ofthe HTL 344 is increased, the HOMO energy level HOMO_(HTL) of the HTL344 is lowered (deep HOMO_(HTL)), so that it is possible to reduce orremove the HOMO energy barrier between the HTL 344 and the EML 350.

the above first aspect, the OLED 300 has a mono-layered HTL 344. Unlikethat aspect, an LED may include a multiple-layered HTL. FIG. 5 is aschematic cross-sectional view illustrating a light emitting diodehaving a normal structure in accordance with another exemplary aspect ofthe present disclosure. As illustrated in FIG. 5, the light emittingdiode (LED) 400 in accordance with the second aspect of the presentdisclosure includes a first electrode 410, a second electrode 420 facingthe first electrode 410 and an emission layer 430 as an emitting unitdisposed between the first and second electrodes 410 and 420. Theemissive layer 430 includes an emitting material layer (EML) 450disposed between the first and second electrodes 410 and 420, a firstcharge transfer layer (CTL1) 440 disposed between the first electrode410 and the EML 450 and a second charge transfer layer (CTL2) 460disposed between the second electrode and the EML 450.

In the second aspect of the present disclosure, the first electrode 410may be a hole injection electrode and the second electrode 420 may be anelectron injection electrode. The CTL1 440 may be a hole transfer layerand may include a hole injection layer (HIL) 442 and a hole transportlayer (HTL) 444. The EML 450 may include an inorganic luminescentparticles such as QDs and/or QRs or an organic luminous material such anorganic host and an organic dopant. The CTL2 460 may be an electrontransfer layer and may include an electron injection layer (EIL) 462 andan electron transport layer (ETL) 464.

In an alternative aspect, the LED 400 may further include at least onecharge blocking layer such as an electron blocking layer (EBL, notshown) that can control and prevent electron transportations between theHTL 444 and the EML 450 and/or a hole blocking layer (HBL, not shown)that can control and prevent hole transportation between the EML 450 andthe ETL 464. The emission layer 430 may have identical structure as theemission layer 330 except the HTL 444.

In this exemplary aspect, the HTL 444 includes a first hole transportlayer (HTL1) 444 a disposed between the HIL 442 and the EML 450 and asecond hole transport layer (HTL2) 444 b disposed between the HTL1 444 aand the EML 450. Since the organic compound having the structure ofanyone in Chemical Formulae 1 to 4 includes a fused aryl or hetero arylring, the organic compound has a low HOMO energy level. Considering thisproperty, the HTL1 444 a may include other hole transporting materialand the HTL2 444 b may include the organic compound having the structureof anyone in Chemical Formulae 1 to 4.

As an example, the hole transporting material in the HTL1 444 a mayinclude, but are not limited to, an organic material having an aryl orhetero aryl amine moiety, a fluorene moiety and/or a carbazole moiety,each of which shows excellent hole mobility. As an example, the holetransporting material in the HTL1 444 a may include the organic materialhaving the structure of anyone in Chemical Formulae 5 to 8. The organicmaterial having the structure of anyone in Chemical Formulae 5 to 8 mayinclude, but are not limited to, p-TPD, TFB, PVK, PTAA and the likes.

In an alternative aspect, the HTL1 444 a may include another holetransporting material having a non-polymer structure. The holetransporting material having the non-polymer structure in the HTL1 444 amay include, but are not limited to, TPD, spiro-TPD, DOFL-TPD, DOFL-NPB,TTP, HMTPD, TAPC, OTPD,4,4′,4″-tris(N,N-phenyl-3-ethylamino)triphenylamine and the likes.

In one exemplary aspect, the HTL 440 may include the hole transportingmaterial having the structure of anyone in Chemical Formulae 5 to 8 inthe HTL1 444 a and the organic compound having the structure of anyonein Chemical Formulae 1 to 4 in the HTL2 444 b. In this case, the holemobility property of the HTL 444 is increased and a HOMO energy barrierbetween the HTL 444 and the EML 450 can be reduced, which is resultedfrom the low HOMO energy level HOMO_(HTL2) of the HTL2 444 b.Accordingly, the LED 400 can enhance its luminous efficiency and lowerits driving voltage as the holes and electrons are injected into the EML450 in a balanced manner.

In the above aspects, the LEDs 300 and 400 have a normal structure wherethe hole transfer layer is disposed between the first electrode havingrelatively higher work function value and the EML and the electrontransfer layer is disposed between the second electrode havingrelatively lower work function value and the EML. In contrast, a lightemitting diode may have an inverted structure, not the normal structure.FIG. 6 is a schematic cross-sectional view illustrating a light emittingdiode having an inverted structure in accordance with another exemplaryaspect of the present disclosure.

As illustrated in FIG. 6, the light emitting diode 500 in accordancewith the third aspect of the present disclosure include a firstelectrode 510, a second electrode 520 facing the first electrode 510 andan emissive layer 530 as an emitting unit disposed between the first andsecond electrodes 510 and 520. The emissive layer 530 includes anemitting material layer (EML) 550 disposed between the first and secondelectrodes 510 and 520, a first charge transfer layer (CTL1) 540disposed between the first electrode 510 and the EML 550 and a secondcharge transfer layer (CTL2) 560 disposed between the second electrode520 and the EML 550.

The first electrode 510 may be a cathode such as an electron injectionelectrode. As an example, the first electrode 510 may include, but arenot limited to, a doped or undoped metal oxide such as ITO, IZO, ITZO,OCO, SnO₂, In₂O₃, Cd:ZnO, F:SnO₂, In:SnO₂, Ga:SnO₂ and AZO, or metal ornonmetal material such as Ni, Pt, Au, Ag, Ir or CNT, other than theabove-described metal oxide.

The second electrode 520 may be an anode such as a hole injection layer.As an example, the second electrode 520 may include, but are not limitedto, Ca, Ba, Ca/Al, LiF/Ca, LiF/Al, BaF₂/Al, CsF/Al, CaCO₃/Al,BaF₂/Ca/Al, Al, Mg, Au:Mg or Ag:Mg. As an example, each of the firstelectrode 510 and the second electrode 520 may have a thickness of, butare not limited to, about 5 to about 300 nm, and alternatively about 10nm to about 200 nm.

The CTL1 540 may be an electron transfer layer which provides electronsinto the EML 550. In one exemplary aspect, the CTL1 540 may include anelectron injection layer (EIL) 542 disposed adjacently to the firstelectrode 510 between the first electrode 510 and the EML 550, and anelectron transport layer (ETL) 544 disposed adjacently to the EML 550between the first electrode 510 and the EML 550.

The EIL 542 may include, but are not limited to, a metal such as Al, Cd,Cs, Cu, Ga, Ge, In and/or Li, each of which is undoped or doped withfluorine; and/or metal oxide such as TiO₂, ZnO, ZrO, SnO₂, (WO₃ and/orTa₂O₃, each of which is undoped or doped with Al, Mg, In, Li, Ga, Cd, Csor Cu.

The ETL 544 may include an inorganic material or an organic material. Inone exemplary aspect, the ETL 544 may include an inorganic materialhaving excellent charge mobility (i.e. electron mobility) and having aHOMO energy level, or a valence band energy level deeper or lower than aHOMO energy level of the luminous material in the EML 550.

As an example, when the ETL 544 includes an inorganic material, the ETL544 may include, but are not limited to, a metal oxide undoped or dopedwith at least one of Al, Mg, In, Li, Ga, Cd, Cs and Cu; a semiconductorparticle undoped or doped with at least one of Al, Mg, In, Li, Ga, Cd,Cs and Cu; metal nitrides; and combination thereof.

In one exemplary aspect, the metal component of the metal oxide in theETL 544 may be selected from, but are not limited to, zinc (Zn), calcium(Ca), magnesium (Mg), titanium (Ti), tin (Sn), tungsten (W), tantalum(Ta), hafnium (Hf), aluminum (Al), zirconium (Zr), barium (Ba) andcombination thereof. Particularly, the metal oxide may include, but arenot limited to, titanium dioxide (TiO₂), zinc oxide (ZnO), magnesiumzinc oxide (ZnMgO), zirconium oxide (ZrO), tin oxide (SnO₂), tungstenoxide (WO₃), tantalum oxide (Ta₂O₃), hafnium oxide (HfO₃), aluminumoxide (Al₂O₃), barium titanium oxide (BaTiO₃), and barium zirconiumoxide (BaZrO₃), each of which is undoped or doped with Al, Mg, In, Li,Ga, Cd, Cs or Cu.

Other inorganic material in the ETL 544 may include, but are not limitedto, a semiconductor particle such as CdS, ZnSe, ZnS, each of which isundoped or doped with Al, Mg, In, Li, Ga, Cd, Cs or Cu; nitrides such asSi₃N₄; and combination thereof.

In another exemplary aspect, when the ETL 544 includes an organicmaterial, the ETL 544 may include, but are not limited to, oxazole-basedcompounds, isooxazole-based compounds, triazole-based compounds,isotriazole-based compounds, oxadiazole-based compounds,thiadiazole-based compounds, phenanthroline-based compounds,perylene-based compound, benzoxazole-based compounds,benzothiazole-based compounds, benzimidazole-based compounds,triazine-based compounds and/or aluminum complexes. Particularly, theorganic compound of the ETL 544 may include, but are not limited to,TAZ, BCP, TPBi, Alq₃, Balq, Salq and combination thereof.

The CTL1 540 may have a mono-layered structure having only the ETL 544.Alternatively, the CTL1 540 may have a mono-layered structure of ETL 544including a blend of the above-described electron-transporting inorganicmaterial with cesium carbonate.

The CTL1 540, which includes the EIL 542 and/or the ETL 544, may belaminated by any vacuum deposition process such as vacuum vapordeposition and sputtering, or by any solution process such as spincoating, drop coating, dip coating, spray coating, roll coating, flowcoating, casting, screen printing and inkjet printing, or combinationthereof. As an example, each of the EIL 542 and the ETL 544 may have athickness, but are not limited to, between about 10 nm and about 200 nm,and alternatively about 10 nm and 100 nm.

The EML 550 may include inorganic luminescent particles or organicluminescent material. As an example, the EML 550 may include inorganicluminescent particles such as quantum dots (QDs) or quantum rods (QRs).The QDs or QRs may have a single-layered structure or a multiple-layeredheterologous structure, i.e. core/shell structure. In this case, each ofthe core and the shell may have single layer or multiple layers,respectively. As an example, the QDs or the QRs may have a type Icore/shell structure, a type II core/shell structure or a reverse type Icore/shell structure.

In one exemplary aspect, each of the core and the shell may include, butare not limited to, a semiconductor nanocrystals and/or metal oxidenanocrystals having quantum confinement effect. For example, thesemiconductor nanocrystals of the core and the shell may be selectedfrom the group, but are not limited to, consisting of Group II-VIcompound semiconductor nanocrystals, Group III-V compound semiconductornanocrystals, Group IV-VI compound semiconductor nanocrystals, GroupI-III-VI compound semiconductor nanocrystals and combination thereof.

Particularly, Group II-VI compound semiconductor nanocrystals of thecore and/or the shell may be selected from the group, but are notlimited to, consisting of MgS, MgSe, MgTe, CaS, CaSe, CaTe, SrS, SrSe,SrTe, BaS, BaSe, BaTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeSe, ZnO, CdS, CdSe,CdTe, CdSeS, CdZnS, CdSeTe, CdO, HgS, HgSe, HgTe, CdZnTe, HgCdTe,HgZnSe, HgZnTe, CdS/ZnS, CdS/ZnSe, CdSe/ZnS, CdSe/ZnSe, ZnSe/ZnS,ZnS/CdSZnS, CdS/CdZnS/ZnS, ZnS/ZnSe/CdSe and combination thereof.

Group III-V compound semiconductor nanocrystals of the core and/or shellmay be selected from the group, but are not limited to, consisting ofAN, AlP, AlAs, AlSb, GaN, GaP, Ga₂O₃, GaAs, GaSb, InN, In₂O₃, InP, InAs,InSb, AlGaAs, InGaAs, InGaP, AlInAs, AlInSb, GaAsN, GaAsP, GaAsSb,AlGaN, AlGaP, InGaN, InAsSb, InGaSb, AlGaInP, AlGaAsP, InGaAsP,InGaAsSb, InAsSbP, AlInAsP, AlGaAsN, InGaAsN, InAlAsN, GaAsSbN,GaInNAsSb and combination thereof.

Group IV-VI compound semiconductor nanocrystals of the core and/or shellmay be selected from the group, but are not limited to, consisting ofTiO₂, SnO₂, SnS, SnS₂, SnTe, PbO, PbO₂, PbS, PbSe, PbTe, PbSnTe andcombination thereof. Also, Group I-III-VI compound semiconductornanocrystals of the core and/or shell may be selected from the group,but are not limited to, AgGaS₂, AgGaSe₂, AgGaTe₂, AgInS₂, CuInS₂,CuInSe₂, Cu₂SnS₃, CuGaS₂, CuGaSe₂ and combination thereof.Alternatively, each of the core and the shell may independently includemultiple layers each of which has different Groups compoundsemiconductor nanocrystals, e.g., Group II-VI compound semiconductornanocrystals and Group III-V compound semiconductor nanocrystals such asInP/ZnS, InP/ZnSe, GaP/ZnS, and the likes, respectively.

In another aspect, the metal oxide nanocrystals of the core and/or shellmay include, but are not limited to, Group II or Group III metal oxidenanocrystals. As an example, the metal oxide nanocrystals of the coreand/or the shell may be selected from the group, but are not limited to,MgO, CaO, SrO, BaO, Al₂O₃ and combination thereof.

The semiconductor nanocrystals of the core and/or the shell may be dopedwith a rare earth element such as Eu, Er, Tb, Tm, Dy or an arbitrarycombination thereof or may be doped with a transition metal element suchas Mn, Cu, Ag, Al or an arbitrary combination thereof.

As an example, the core in QDs or QRs may include, but are not limitedto, ZnSe, ZnTe, CdSe, CdTe, InP, ZnCdS, Cu_(x)In_(1-x)S,Cu_(x)In_(1-x)Se, Ag_(x)In_(1-x)S and combination thereof. The shell inQDs or QRs may include, but are not limited to, ZnS, GaP, CdS, ZnSe,CdS/ZnS, ZnSe/ZnS, ZnS/ZnSe/CdSe, GaP/ZnS, CdS/CdZnS/ZnS, ZnS/CdSZnS,Cd_(x)Zn_(1-x)S and combination thereof.

In another exemplary aspect, the inorganic luminescent particle mayinclude, but are not limited to, alloy QD or alloy QR such as homogenousalloy QD or QR or gradient alloy QD or QR, e.g. CdS_(x)Se_(1-x),CdSe_(x)Te_(1-x), Cd Cd_(x)Zn_(1-x)S, Zn_(x)Cd_(1-x)Se, Cu_(x)In_(1-x)S,Cu_(x)In_(1-x)Se, Ag_(x)In_(1-x)S.

When the EML 550 includes inorganic luminescent particles such as QDsand/or QRs, the EML 550 may be laminated through any solution process,i.e. coating the dispersion solution, which contains inorganicluminescent particles dissolved in a solvent, on the CTL1 540, forexample the HTL 544, and evaporating the solvent. In one aspect, the EML550 may be laminated on the CTL1 540 using any solution process such asspin coating, drop coating, dip coating, spray coating, roll coating,flow coating casting, screen printing and inkjet printing, or acombination thereof.

In an alternative aspect, the EML 550 may include an organic luminousmaterial. The organic luminous material is not limited to specificorganic luminous material. As an example, the EML 550 may include anorganic luminous material that emits red (R), green (G) or blue (B)light, and may include fluorescent material or phosphorescent material.As an example, the organic luminous material in the EML 550 may includea host and a dopant. When the organic luminous material constitutes ahost-dopant system, the EML 550 may include the dopant, but are notlimited to, about 1 to about 50% by weight, and alternatively about 1 toabout 30% by weight. Alternatively, when the EML 550 includes an organicluminous material, the EML 550 may include a delayed fluorescentmaterial.

When the EML 550 includes an organic luminous material, the EML 550 maybe laminated by any vacuum deposition process such as vacuum vapordeposition and sputtering, or by any solution process such as spincoating, drop coating, dip coating, spray coating, roll coating, flowcoating, casting, screen printing and inkjet printing, or a combinationthereof. For example, the EML 550 may have a thickness, but are notlimited to, between about 5 nm and about 300 nm, alternatively about 10nm and about 200 nm.

The CTL2 560 may be a hole transfer layer which provides holes into theEML 550. In one exemplary aspect, the CTL2 560 may include a holeinjection layer (HIL) 562 disposed adjacently to the second electrode520 between the second electrode 520 and the EML 550, and a holetransport layer (HTL) 564 disposed adjacently to the EML 550 between thesecond electrode 520 and the EML 550.

The HIL 562 may include, but are not limited to, a material PEDOT:PSS,TDATA doped with F4-TCNQ, p-doped phthalocyanine such as ZnPc doped withF4-TCNQ, α-NPD doped with F4-TCNQ, HAT-CN and combination thereof. As anexample, the HIL 562 may include the dopant such as F4-TCNQ about 1 toabout 30% by weight. The HIL 562 may be omitted in compliance with astructure of the LED 500.

The HTL 564 includes the organic compound having the structure of anyonein Chemical Formulae 1 to 4. In one exemplary aspect, the HTL 564 mayinclude only the organic compound having the structure of anyone inChemical Formula 1 to 4. In another exemplary aspect, the organiccompound having the structure of anyone in Chemical Formulae 1 to 4 maybe used as dopant in the HTL 564. In this case, the HTL 564 includesother hole transporting material as a host.

The hole transporting host in the HTL 564 is not limited to specificmaterial. In one exemplary aspect, the hole transporting host may bepolymer material having an aryl or hetero aryl amine moiety, a fluorenemoiety and/or a carbazole moiety, each of which has an excellent holemobility. As an example, the hole transporting host in the HTL 564 mayinclude, but are not limited to, any organic polymer material having thestructure of anyone in Chemical Formulae 5 to 8. The organic polymermaterial which can be used as the hole transporting material in the HTL564 may include, but are not limited to, p-TPD, TFB, PVK, PTAA, and thelikes.

In another alternative aspect, the hole transporting host in the HTL 564may be a non-polymer organic material. The hole transporting host ofnon-polymer structure may include, but are not limited to TPD,spiro-TPD, DOFL-TPD, DOFL-NPB, TTP, HMTPD, TAPC, OTPD,4,4′,4″-tris(N,N-phenyl-3-methhylphenylamino)triphenylamine, and thelikes.

In FIG. 6, while the CTL2 560 as a hole transfer layer is divided intothe HIL 562 and the HTL 564, the CTL2 560 may have a mono-layeredstructure. For example, the CTL2 560 may include only the HTL 564without the HIL 562 or may include the above-mentioned hole transportingmaterial doped with the hole injection material (e.g. PEDOT:PSS).

The CTL2 560 including the HIL 562 and the HTL 564 may be laminated byany vacuum deposition process such as vacuum vapor deposition andsputtering, or by any solution process such as spin coating, dropcoating, dip coating, spray coating, roll coating, flow coating,casting, screen printing and inkjet printing, or a combination thereof.For example, each of the HIL 562 and the HTL 564 may have a thickness,but are not limited to, between about 10 nm and 200 nm, andalternatively about 10 nm and 100 nm.

The LED 500 in accordance with the third aspect of the presentdisclosure may further include at least one exciton blocking layerdisposed adjacently to the EML 550. For example, the LED 500 may furtherinclude an electron blocking layer (EBL, not shown) that can control andprevent electron transportations between the EML 550 and the HTL 564and/or a hole blocking layer (HBL, not shown) that can control andprevent hole transportations between the ETL 544 and the EML 550.

The HTL 564 constituting the CTL2 560 disposed between the secondelectrode 520 and the EML 550 in the LED in accordance with the thirdaspect of the present disclosure includes the organic compound havingthe structure of anyone in Chemical Formulae 1 to 4. As described above,the organic compound having the structure of anyone in Chemical Formulae1 to 4 has a very low HOMO energy level HOMO_(HTL). Accordingly, as theenergy level bandgap “Δ′G_(H)” between the HOMO energy level HOMO_(HTL)of the HTL 564 and the HOMO energy level HOMO_(EML) of the EML 550 isgreatly reduced, it is possible to reduce or minimize the energy barrierbetween the HTL 564 and the EML 550, as illustrated in FIG. 7, which isa schematic diagram illustrating energy levels among materials inemissive layers between electrodes in accordance with another exemplaryaspect of the present disclosure.

In other words, when the organic compound having the structure of anyonein Chemical Formulae 1 to 4 is applied into the HTL 564, the energylevel bandgap “Δ′G_(H)” between the HOMO energy level HOMO_(HTL) of theHTL 564 and the HOMO energy level HOMO_(EML) of the EML 550 issubstantially the same as the energy level bandgap “ΔG_(L)” between theLUMO energy level LUMO_(ETL) or conduction band energy level CB_(ETL) ofthe ETL 544 and the LUMO energy level LUMO_(EML) of the EML 550. Sincethe electrons “{circle around (e)}⁻” and the holes “{circle around(h)}⁺” can be injected into the EML in a balanced manner to formexcitons, the amount of electrons that is quenched without formingexcitons can be reduced or minimized. In addition, the electrons“{circle around (e)}⁻” and holes “{circle around (h)}⁺” are recombinedwith each other in the luminous material within the EML 550, not atinterfaces between the EML 550 and adjacent CTL (e.g. HTL or ETL).Accordingly, the LED 500 can maximize its luminous efficiency and lowerpower consumption since it can be driven at lower voltage.

An LED having an inverted structure may have a multiple-layered holetransport layer. FIG. 8 is a schematic cross-sectional view illustratinga light emitting diode having an inverted structure in accordance withstill another exemplary aspect of the present disclosure.

As illustrated in FIG. 8, the light emitting diode (LED) 600 inaccordance with the fourth aspect of the present disclosure includes afirst electrode 610, a second electrode 620 facing the first electrode610 and an emission layer 630 as an emitting unit disposed between thefirst and second electrodes 610 and 620. The emissive layer 630 includesan emitting material layer (EML) 650 disposed between the first andsecond electrodes 610 and 620, a first charge transfer layer (CTL1) 640disposed between the first electrode 610 and the EML 650 and a secondcharge transfer layer (CTL2) 660 disposed between the second electrodeand the EML 650.

In the fourth aspect of the present disclosure, the first electrode 610may an electron injection electrode and the second electrode 620 may bea hole injection electrode. The CTL1 640 may be an electron transferlayer and may include an electron injection layer (EIL) 642 and anelectron transport layer (ETL) 644. The EML 650 may include an inorganicluminescent particles such as QDs and/or QRs or an organic luminousmaterial such an organic host and an organic dopant. The CTL2 660 may bea hole transfer layer and may include a hole injection layer (HIL) 662and a hole transport layer (HTL) 664.

In an alternative aspect, the LED 600 may further include at least onecharge blocking layer such as an electron blocking layer (EBL, notshown) that can control and prevent electron transportations between theHTL 664 and the EML 650 and/or a hole blocking layer (HBL, not shown)that can control and prevent hole transportation between the EML 650 andthe ETL 644. The emission layer 630 may have identical structure as theemission layer 530 except the HTL 664.

In this exemplary aspect, the HTL 664 includes a first hole transportlayer (HTL1) 664 a disposed between the HIL 662 and the EML 650 and asecond hole transport layer (HTL2) 664 b disposed between the HTL1 664 aand the EML 650. As an example, the HTL1 664 a may include other holetransporting material and the HTL2 664 b may include the organiccompound having the structure of anyone in Chemical Formulae 1 to 4.

As an example, the hole transporting material in the HTL1 664 a mayinclude, but are not limited to, an organic material having an aryl orhetero aryl amine moiety, a fluorene moiety and/or a carbazole moiety,each of which shows excellent hole mobility. As an example, the holetransporting material in the HTL1 664 a may include the organic materialhaving the structure of anyone in Chemical Formulae 5 to 8. The organicmaterial having the structure of anyone in Chemical Formulae 5 to 8 mayinclude, but are not limited to, p-TPD, TFB, PVK, PTAA and the likes.

In an alternative aspect, the HTL1 664 a may include another holetransporting material having a non-polymer structure. The holetransporting material having the non-polymer structure in the HTL1 664 amay include, but are not limited to, TPD, spiro-TPD, DOFL-TPD, DOFL-NPB,TTP, HMTPD, TAPC, OTPD,4,4′,4″-tris(N,N-phenyl-3-ethylamino)triphenylamine and the likes.

In one exemplary aspect, the HTL 664 may include the hole transportingmaterial having the structure of anyone in Chemical Formulae 5 to 8 inthe HTL1 664 a and the organic compound having the structure of anyonein Chemical Formulae 1 to 4 in the HTL2 664 b. In this case, the holemobility property of the HTL 664 is increased and a HOMO energy barrierbetween the HTL 664 and the EML 650 can be reduced, which is resultedfrom the low HOMO energy level HOMO_(HTL2) of the HTL2 664 b.Accordingly, the LED 600 can enhance its luminous efficiency and lowerits driving voltage as the holes and electrons are injected into the EML650 in a balanced manner.

Synthesis Example 1: Synthesis of Compound H01

(1) Synthesis of Intermediate 1-1

30.0 g (247 mmol) of 4-ethyl aniline, 45.81 g (248 mmol) of1-bromo-4-ethyl benzene, 1.27 g (2.5 mmol) ofbis(tr-tert-butylphosphine) palladium (0) (Pd(P(t-Bu)₃)₂), and 90 g ofsodium-tert-butoxide (t-BuONa) were placed into a 1000 mL round bottomflask, 300 mL of toluene was added into the flask, and then the solutionwas stirred. After reaction was completed, the solution was extractedwith 500 mL of dichloromethane and water and then distilled underreduced pressure to obtain a solid. Then, the solid was separated andpurified by column chromatography to give 50 g of intermediate 1-1.

(2) Synthesis of Intermediate 1-2

50.0 g (154 mmol) of 3,6-dibromo-9H-carbazole, 33.80 g (154 mmol) ofdi-tert-butyl dicarbonate (BOC), 28 g (231 mmol) of4-dimethylaminopyridine (4-DMAP) and 31.2 g (308 mmol) of triethylaminewere placed into a 1000 mL round bottom flasks, 500 mL oftetrahydrofuran (THF) was added into the flask, and then the solutionwas stirred. After reaction was completed, the solution was extractedwith 500 mL of dichloromethane and water, and then distilled underreduced pressure to obtain a solid. Then, the solid was separated andpurified by column chromatography to give 70 g of intermediate 1-2.

(3) Synthesis of Intermediate 1-3

30.0 g (70.9 mmol) of intermediate 1-2, 17.5 g (78.0 mmol) ofintermediate 1-1, 0.36 g (0.71 mmol) of Pd(P(t-Bu)₃)₂ and 20 g (212mmol) of t-BuONa were placed into a 1000 mL round bottom flasks, 300 mLof toluene was added into the flasks, and then the solution was stirred.After reaction was completed, the solution was extracted with 300 mL ofdichloromethane and water, and then distilled under reduced pressure toobtain a solid. Then, the solid was separated and purified by columnchromatography to give 47 g of intermediate 1-3.

(4) Synthesis of Intermediate 1-4

47 g (65.9 mmol) of the purified intermediate 1-3 and 14.3 g (65.9 mmol)of HCl were added into a mixed solvent of 20 mL of H₂O and 300 mL ofTHF, and then the solution was stirred at room temperature. Afterreaction was completed, the solvent was distilled under reduced pressureto give a solid. The solid was recrystallized with dichloromethane andether to give 50 g of intermediate 1-4.

(5) Synthesis of Intermediate 1-5

20.0 g (69.9 mmol) of 2,2′-dihydroxy-1,1′-binaphthyl and 24.56 g (15mmol) of Br₂ were placed into a 1000 mL round bottom flask, 200 mL ofdichloromethane was added into the flask, and then the solution wasstirred. After reaction was completed, the solution was extracted withexcessive water and then distilled under reduced pressure to obtain acrude product. Then, the crude product was separated and purified bycolumn chromatography to give 28.5 g of intermediated 1-5.

(6) Synthesis of Intermediate 1-6

15.5 g (69.5 mmol) of the purified intermediate 1-5, 21 g (153 mmol) of1-bromobutane and 14.4 g (104 mmol) of K₂CO₃ were placed into a 1000 mLround bottom flask, 150 mL of toluene was added into the flasks, andthen the solution was stirred. After reaction was completed, thesolution was extracted with 300 mL of dichloromethane and water and thendistilled under reduced pressure to obtain a solid. Then, the solid wasseparated and purified by column chromatography to give 35 g ofintermediate 1-6.

(7) Synthesis of Compound H01

10.0 g (18.0 mmol) of intermediate 1-6, 15.45 g (40.0 mmol) ofintermediate 1-4, 0.28 g (0.50 mmol) of Pd(P(t-Bu)₃)₂ and 30 g oft-BuONa were placed into a 1000 mL round bottom flasks, 150 mL oftoluene was added into the flasks, and then the solution was stirred.After reaction was completed, the solution was extracted with 300 mL ofdichloromethane and water and then distilled under reduced pressure toobtain a solid. Then, the solid was separated and purified by columnchromatography to give 21.1 g of Compound H01.

Synthesis Example 2: Synthesis of Compound H02

20.0 g (48.7 mmol) of 6,6-dibromo-1,1′-binaphthyl, 65.8 g (107.1 mmol)of intermediate 1-4, 0.50 g (1.46 mmol) of Pd(P(t-Bu)₃)₂ and 60 g (146mmol) of t-BuONa were placed into a 500 mL round bottom flasks, 500 mLof toluene was added into the flasks, and then the solution was stirred.After reaction was completed, the solution was distilled under reducedpressure to remove the solvent, extracted with 300 mL of dichloromethaneand water and then distilled under reduced pressure to obtain a solid.Then, the solid was separated and purified by column chromatography togive 35 g of Compound H02.

Synthesis Example 3: Synthesis of Compound H03

(1) Synthesis of Intermediate 3-1

30.0 g (70.9 mmol) of intermediate 1-2, 17.4 g (78.0 mmol) of3,6-diethyl-9H-carbazole, 0.36 g (0.71 mmol) of Pd(P(t-Bu)₃)₂ and 20 g(212 mmol) of t-BuONa were placed into a 1000 mL round bottom flasks,300 mL of toluene was added into the flasks, and then the solution wasstirred. After reaction was completed, the solution was extracted with300 mL of dichloromethane and water, and then distilled under reducedpressure to obtain a solid. Then, the solid was separated and purifiedby column chromatography to give 50 g of intermediate 3-1.

(2) Synthesis of Intermediate 3-2

50 g (70.5 mmol) of the purified intermediate 3-1 and 15.5 g (70.5 mmol)of HCl were added into a mixed solvent of 20 mL of H₂O and 300 mL ofTHF, and then the solution was stirred at room temperature. Afterreaction was completed, the solvent was distilled under reduced pressureto give a solid. The solid was recrystallized with dichloromethane andether to give 47 g of intermediate 3-2.

(3) Synthesis of Compound H03

20.0 g (48.7 mmol) of 6,6′-dibromo-1,1′-binaphthyl, 62.4 g (58.6 mmol)of intermediate 3-2, 0.50 g (1.46 mmol) of Pd(P(t-Bu)₃)₂ and 60 g (146mmol) of t-BuONa were placed into a 500 mL round bottom flasks, 500 mLof toluene was added into the flasks, and then the solution was stirred.After reaction was completed, the solution was distilled under reducedpressure to remove the solvent, was extracted with 300 mL ofdichloromethane and water, and then distilled under reduced pressure togive a solid. Then, the solid was separated and purified by columnchromatography to give 35 of Compound H03.

Synthesis Example 4: Synthesis of Compound H12

(1) Synthesis of Intermediate 4-1

130 g (777 mmol) of carbazole, 165 g (855 mmol) of 1-bromo-2-ethylhexaneand 20.5 g (855 mmol) of sodium hydride were placed into a 2000 mL roundbottom flask, 1300 mL of THF was added into the flask, and then thesolution was stirred. After reaction was completed, the solution wasextracted with dichloromethane and water and then distilled underreduced pressure to obtain a solid. Then, the solid was separated andpurified by column chromatography to give 215 g of intermediate 4-1.

(2) Synthesis of Intermediate 4-2

108 g (388 mmol) of the purified intermediate 4-1 and 76 g (427 mmol) ofN-bromosuccinimide were placed into a 2000 mL round bottom flask, 1100mL of dichloromethane was added into the flask, and then the solutionwas stirred. After reaction was completed, the solution was extractedwith water and distilled under reduced pressure to obtain a solid. Then,the solid was separated and purified by column chromatography to give119 g of intermediate 4-2.

(3) Synthesis of Intermediate 4-4

108 g (389 mmol) of intermediate 4-2 and 76.1 g (178 mmol) ofbis(pinacolato)diboron were placed into a 1000 mL round bottom flask,700 mL of dichloromethane was added into the flask, and then thesolution was stirred. After reaction was completed, the solution wasextracted with dichloromethane and water and then distilled underreduced pressure to give intermediate 4-3. 39.4 g (97.2 mmol) of theobtained intermediate 4-3, 30.4 g (107 mmol) of 1-bromo-4-iodobenzene,1.12 g (0.97 mmol) of tetrakis(triphenylphosphine) palladium (0)(Pd(pph₃)₄) and 295 g of 1M K₂CO₃ was dissolved in 600 mL of THF, andthe solution was heated with stirring. After reaction was completed, thesolution was extracted with dichloromethane and water and then distilledunder reduced pressure to obtain a solid. Then, the solid was separatedand purified by column chromatography to give 40 g of intermediated 4-4.

(4) Synthesis of Intermediate 4-5

16 g (28.7 mmol) of intermediate 1-6, 16.2 g (28.7 mmol) ofbis(pinacolato)diboron, 0.47 g (0.57 mmol) of[1,1′-bis(diphenylphosphino)ferrocene]dichloro palladium (II) complexwith dichloromethane (Pd(dppf)Cl₂.DCM) and 5.63 g (57.4 mmol) ofpotassium acetate (KOAc) were placed into a 500 mL round bottom flasks,200 mL of 1,4-dioxane was added into the flasks, and then the solutionwas stirred. After reaction was completed, the solution was distilledunder reduced pressure to remove the reaction solvent, extracted withdichloromethane and water and distilled under reduced pressure again toobtain a crude product. Then, the crude product was separated andpurified by column chromatography to give 15 g of intermediate 4-5.

(5) Synthesis of Compound H12

9.3 g (14.3 mmol) of intermediate 4-5, 13.7 g (31.6 mmol) ofintermediate 4-4, 0.83 g (0.7 mmol) of Pd(pph₃)₄ and 140 g of 2M K₂CO₃were placed into a 1000 mL round bottom flasks, 300 mL of dioxane wasadded into the flask, and then the solution was heated with stirring.After reaction was completed, the solution was extracted withdichloromethane and water and then distilled under reduced pressure toobtain a solid. Then, the solid was separated and purified by columnchromatography to give 14.5 g of Compound H12.

Synthesis Example 5: Synthesis of Compound H13

12.5 g (18.5 mmol) of intermediate 4-5, 16.0 g (37.0 mmol) of[9-(4-bromophenyl)]-3,6-di-tert-butyl-9H-carbazole, 1.08 g (0.91 mmol)of Pd(pph₃)₄ and 156 g of 2M K₂CO₃ were placed into a 1000 mL roundbottom flasks, 500 mL of dioxane was added into the flask, and then thesolution was heated with stirring. After reaction was completed, thesolution was extracted with dichloromethane and water and then distilledunder reduced pressure to obtain a solid. Then, the solid was separatedand purified by column chromatography to give 18 g of Compound H13.

Example 1: Fabrication of Light Emitting Diode (LED)

A light emitting diode was fabricated applying Compound H01 synthesizedin the Synthesis Example 1 into a hole transport layer. An ITO-glass waspatterned to have luminous area 3 mm×3 mm and washed. And an emissivelayer and cathode were laminated as the following order:

a hole injection layer (HIL) (PEDOT:PSS; spin coating (5000 rpm) andheating for 30 minutes at 150° C.; 20 to 40 nm); a hole transport layer(HTL) (Compound H01; spin coating (4000 rpm) in toluene (8 mg/mL) andheating for 30 minutes at 170° C.; 10 to 30 nm); an emitting materiallayer (EML) (red quantum dot InP/ZnSe/ZnS; spin coating (2000 rpm) inhexane (10 mg/mL) and heating for 1 hour at 80° C.; 10 to 30 nm); anelectron transport layer (ETL) (ZnO; spin coating (4000 rpm) in ethanol(25 mg/mL) and heating for 30 minutes at 80° C.; 30 to 50 nm).

And then, the ITO-glass substrate having the laminated charge transferlayers and the EML was transferred to a vacuum chamber, where a cathode(Al; 80 nm) was deposited under 10⁻⁶ Torr. After depositing the cathode,the LED was transferred from the vacuum chamber to a dry box for filmformation, followed by encapsulation using UV-curable epoxy and moisturegetter. The manufacture organic light emitting diode had an emissionarea of 9 mm².

Examples 2 to 5: Manufacture of LED

A LED was manufactured by repeating the same process and using the samematerial as Example 1, except using the Compound H02 (Example 2), theCompound H03 (Example 3), the Compound H12 (Example 4) or the CompoundH13 (Example 5) in place of the Compound H01 as a hole transportingmaterial in the HTL.

Comparative Examples 1 and 2: Manufacture of LED

A LED was manufactured by repeating the same process and using the samematerial as Example 1, except using p-TPD (Comparative Example 1,Ref. 1) or TFB (Comparative Example, Ref. 2) in place of the Compound 1as a hole material in the HTL.

Experimental Example 1: Measurement of Luminous Properties of OLED

Each of the light emitting diode manufactured by Examples 1 to 5 andRef. 1 to 2 was connected to an external power source, and luminousproperties for all the diodes were evaluated using a constant currentsource (KEITHLEY) and a photometer PR650 at room temperature. Inparticular, driving voltage (V), current efficiency (cd/A), externalquantum efficiency (EQE; %) and color coordinates for emissionwavelength at a current density of 10 mA/cm² of the light emittingdiodes of Examples 1 to 5 and Ref. 1 to 2 were measured. The resultsthereof are shown in the following Table 1.

TABLE 1 Luminous Properties LED 10 mA/cm² Sample HTL V cd/A EQE (%) CIExCIEy Ref. 1 p-TPD 9.2 0.75 1.13 0.675 0.320 Ref. 2 TFB 7.1 1.67 2.150.662 0.321 Example 1 H01 5.42 4.09 5.80 0.678 0.3201 Example 2 H02 5.393.67 5.35 0.6774 0.3195 Example 3 H03 5.43 4.02 5.66 0.6783 0.3202Example 4 H12 4.4 2.84 4.22 0.681 0.316 Example 5 H13 4.4 3.54 5.170.678 0.316

As indicated in Table 1, the LED using the organic compound in the HTLas Examples 1 to 5 has enhanced luminous efficiency compared with theLED using the prior art hole transporting materials, p-TPD or TFB in theHTL as Ref. 1 and Ref. 2. Particularly, compared with the LED using theprior art hole transporting material as the Refs. 1 and 2, the LED usingthe organic compound in the HTL as Examples 1 to 5 reduced drivingvoltage up to 52.2%, and improved current efficiency up to 445.3% andEQE up to 400.9%. The LED manufactured in Examples 1 to 5 showedsubstantially identical color coordinates to the LED manufactured inRefs. 1 and 2, which indicate that it is possible to realize desiredluminescence by applying the organic compounds to the HTL.

Examples 6 to 10: Manufacture of LED

A LED was manufactured by repeating the same process and using the samematerial as Example 1, except using TFB:H01 (host:dopant, 1:1 by volumeratio) (Example 6), TFB:H02 (host:dopant, 1:1 by volume ratio) (Example7), TFB:H03 (host:dopant, 1:1 by volume ratio) (Example 8), TFB:H12(host:dopant; 1:1 by volume ratio) (Example 9) or TFB:H13 (host:dopant,1:1 by volume ration) (Example 10) in place of using only the CompoundH01 as a hole transporting material in the HTL.

Comparative Examples 3 and 4: Manufacture of LED

A LED was manufactured by repeating the same process and using the samematerial as Example 1, except using TFB:CBP(4,4′-Bis(N-carbazolyl)-1,1′-biphenyl) (host:dopant, 1:1 by volumeratio) (Comparative Example 3, Ref. 3) or TFB:TCTA(Tris(3-carbazolyl-9-yl-phenyl)amine) (host:dopant, 1:1 by volume ratio)(Comparative Example 4, Ref. 4) in place of using only the Compound H01as a hole transporting material of the HTL.

Experimental Example 2: Measurement of Luminous Properties of OLED

Luminous properties for LEDs manufactured in Examples 4 to 6 and Refs. 1to 4 were measured as the same process as Experimental Example 1. Themeasurement results are shown in the following Table 2.

TABLE 2 Luminous Properties LED 10 mA/cm² Sample HTL V cd/A EQE (%) CIExCIEy Ref. 1 p-TPD 9.2 0.75 1.13 0.675 0.320 Ref. 2 TFB 7.1 1.67 2.150.662 0.321 Ref. 3 TFB:CBP 10.9 0.56 0.85 0.678 0.316 Ref. 4 TFB:TCTA10.8 0.88 1.52 0.677 0.319 Example 6 TFB:H01 4.42 4.83 5.80 0.678 0.316Example 7 TFB:H02 4.77 4.36 5.91 0.680 0.318 Example 8 TFB:H03 4.83 4.085.65 0.681 0.318 Example 9 TFB:H12 4.30 4.36 5.65 0.681 0.316 Example 10TFB:H13 4.0 4.39 5.91 0.680 0.3116

As indicated in Table 2, the LED using the organic compound as a dopantin the HTL as Examples 6 to 10 has enhanced luminous efficiency comparedwith the LED using only the prior art hole transporting material orusing the prior art hole transporting materials as a dopant in the HTLas Ref. 1 to Ref. 4. Particularly, compared with the LED using the priorart hole transporting material as the Refs. 1 and 2, the LED using theorganic compound as a dopant in the HTL as Examples 6 to 10 reduceddriving voltage up to 56.5%, and improved current efficiency up to544.0% and EQE up to 423.3%. In addition, compared with the LED usingthe prior art hole transporting material as a dopant in the HTL as theRefs. 3 and 4, the LED using the organic compound as a dopant in the HTLas Examples 6 to 10 reduced driving voltage up to 63.3%, and improvedcurrent efficiency up to 762.5% and EQE up to 595.3%. The LEDmanufactured in Examples 6 to 10 showed substantially identical colorcoordinates to the LED manufactured in Refs. 1 to 4, which indicate thatit is possible to realize desired luminescence by applying the organiccompounds to the HTL.

Considering those results in the Experimental Examples 1 and 2, it ispossible to realize a LED and a light emitting device having low drivingvoltage as well as enhanced luminous efficiency and quantum efficiencyby applying the organic compound synthesized in accordance with thepresent disclosure to the HTL.

While the present disclosure has been described with reference toexemplary aspects and examples, these aspects and examples are notintended to limit the scope of the present disclosure. Rather, it willbe apparent to those skilled in the art that various modifications andvariations can be made in the present disclosure without departing fromthe spirit or scope of the disclosure. Thus, it is intended that thepresent disclosure covers the modifications and variations of thepresent disclosure provided they come within the scope of the appendedclaims and their equivalents.

The various aspects described above can be combined to provide furtheraspects. All of the U.S. patents, U.S. patent application publications,U.S. patent applications, foreign patents, foreign patent applicationsand non-patent publications referred to in this specification and/orlisted in the Application Data Sheet are incorporated herein byreference, in their entirety. Aspects of the aspects can be modified, ifnecessary to employ concepts of the various patents, applications andpublications to provide yet further aspects.

These and other changes can be made to the aspects in light of the abovedetailed description. In general, in the following claims, the termsused should not be construed to limit the claims to the specific aspectsdisclosed in the specification and the claims, but should be construedto include all possible aspects along with the full scope of equivalentsto which such claims are entitled. Accordingly, the claims are notlimited by the disclosure.

What is claimed is:
 1. An organic compound having the followingstructure of Chemical Formula 1:

wherein each of R₁ and R₂ is independently protium, deuterium, tritium,linear or branched C₁˜C₂₀ alkyl group or C₁˜C₂₀ alkoxy group; each of aand b is independently an integer of 1 to 3; each of Ar₁ and Ar₂ isindependently C₄˜C₃₀ hetero aryl group or nitrogen (N), when each of Ar₁and Ar₂ is independently C₄˜C₃₀ hetero aryl group, each of R₃ and R₄ isindependently linear or branched C₁˜C₁₀ alkyl group, C₅˜C₃₀ aryl aminogroup unsubstituted or substituted with linear or branched C₁˜C₁₀ alkylgroup, C₄˜C₃₀ hetero aryl amino group unsubstituted or substituted withlinear or branched C₁˜C₁₀ alkyl group, C₅˜C₃₀ aryl group unsubstitutedor substituted with a group selected from the group consisting of linearor branched C₁˜C₁₀ alkyl group, C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero arylgroup and combination thereof, or C₄˜C₃₀ hetero aryl group unsubstitutedor substituted with a group selected from the group consisting of linearor branched C₁˜C₁₀ alkyl group, C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero arylgroup and combination thereof, and each of c and d is independently anumber of substituents R₃ and R₄ and an integer of 1 to 3, when each ofAr₁ and Ar₂ is independently nitrogen (N), each of R₃ and R₄ isindependently C₅˜C₃₀ aryl group unsubstituted or substituted with agroup selected from the group consisting of linear or branched C₁˜C₁₀alkyl group, C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero aryl group and combinationthereof, or C₄˜C₃₀ hetero aryl group unsubstituted or substituted with agroup selected from the group consisting of linear or branched C₁˜C₁₀alkyl group, C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero aryl group and combinationthereof, and each of c and d is a number of substituents and 2; each ofL₁ and L₂ is independently unsubstituted or substituted C₅˜C₃₀ arylenegroup or C₄˜C₃₀ hetero arylene group; and each of m and n isindependently integer of 0 or
 1. 2. The organic compound of claim 1,wherein the organic compound has the following structure of ChemicalFormula 2:

wherein each of R₁₁ and R₁₂ is independently protium, deuterium,tritium, linear or branched C₁˜C₁₀ alkyl group or C₁˜C₁₀ alkoxy group;each of Ar_(a) and Ar₄ is independently linear or branched C₁˜C₁₀ alkylgroup, C₁₀˜C₃₀ fused hetero aryl group; each of R₁₃ and R₁₄ isindependently C₅˜C₃₀ aryl amino group unsubstituted or substituted withlinear or branched C₁˜C₁₀ alkyl group, C₄˜C₃₀ hetero aryl amino groupunsubstituted or substituted with linear or branched C₁˜C₁₀ alkyl group,C₅˜C₃₀ aryl group unsubstituted or substituted with a group selectedfrom the group consisting of linear or branched C₁˜C₁₀ alkyl group,C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero aryl group and combination thereof; orC₄˜C₃₀ hetero aryl group unsubstituted or substituted with a groupselected from the group consisting of linear or branched C₁˜C₁₀ alkylgroup, C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero aryl group and combinationthereof; each of o and p is independently a number of substituents, R₁₃and R₁₄ and an integer of 1 to 2; and each of m and n is identical asdefined in Chemical Formula
 1. 3. The organic compound of claim 1,wherein the organic compound has the following structure of ChemicalFormula 3:

wherein each of R₂₁ and R₂₂ is independently protium, deuterium,tritium, linear or branched C₁˜C₁₀ alkyl group or C₁˜C₁₀ alkoxy group;each of R₂₃ to R₂₆ is independently C₅˜C₃₀ aryl group unsubstituted orsubstituted with a group selected from the group consisting of linear orbranched C₁˜C₁₀ alkyl group, C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero aryl groupand combination thereof; or C₄˜C₃₀ hetero aryl group unsubstituted orsubstituted with a group selected from the group consisting of linear orbranched C₁˜C₁₀ alkyl group, C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero aryl groupand combination thereof, and each of m and n is identical as defined inChemical Formula
 1. 4. The organic compound of claim 1, wherein theorganic compound includes anyone having the following structure ofChemical Formula
 4.


5. A light emitting diode, comprising: first and second electrodesfacing each other; and an emissive layer between the first and secondelectrodes and including a hole transfer layer, wherein the holetransfer layer includes an organic compound having the followingstructure of Chemical Formula 1:

wherein each of R₁ and R₂ is independently protium, deuterium, tritium,linear or branched C₁˜C₂₀ alkyl group or C₁˜C₂₀ alkoxy group; each of aand b is independently an integer of 1 to 3; each of Ar₁ and Ar_(e) isindependently C₄˜C₃₀ hetero aryl group or nitrogen (N), when each of Ar₁and Ar₂ is independently C₄˜C₃₀ hetero aryl group, each of R₃ and R₄ isindependently linear or branched C₁˜C₁₀ alkyl group, C₅˜C₃₀ aryl aminogroup unsubstituted or substituted with linear or branched C₁˜C₁₀ alkylgroup, C₄˜C₃₀ hetero aryl amino group unsubstituted or substituted withlinear or branched C₁˜C₁₀ alkyl group, C₅˜C₃₀ aryl group unsubstitutedor substituted with a group selected from the group consisting of linearor branched C₁˜C₁₀ alkyl group, C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero arylgroup and combination thereof, or C₄˜C₃₀ hetero aryl group unsubstitutedor substituted with a group selected from the group consisting of linearor branched C₁˜C₁₀ alkyl group, C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero arylgroup and combination thereof, and each of c and d is independently anumber of substituents R₃ and R₄ and an integer of 1 to 3, when each ofAr₁ and Ar₂ is independently nitrogen (N), each of R₃ and R₄ isindependently C₅˜C₃₀ aryl group unsubstituted or substituted with agroup selected from the group consisting of linear or branched C₁˜C₁₀alkyl group, C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero aryl group and combinationthereof, or C₄˜C₃₀ hetero aryl group unsubstituted or substituted with agroup selected from the group consisting of linear or branched C₁˜C₁₀alkyl group, C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero aryl group and combinationthereof, and each of c and d is a number of substituents and 2; each ofL₁ and L₂ is independently unsubstituted or substituted C₅˜C₃₀ arylenegroup or C₄˜C₃₀ hetero arylene group; and each of m and n isindependently integer of 0 or
 1. 6. The light emitting diode of claim 5,wherein the organic compound has the following structure of ChemicalFormula 2:

wherein each of R₁₁ and R₁₂ is independently protium, deuterium,tritium, linear or branched C₁˜C₁₀ alkyl group or C₁˜C₁₀ alkoxy group;each of Ar_(a) and Ar₄ is independently C₁₀˜C₃₀ fused hetero aryl group;each of R₁₃ and R₁₄ is independently linear or branched C₁˜C₁₀ alkylgroup, C₅˜C₃₀ aryl amino group unsubstituted or substituted with linearor branched C₁˜C₁₀ alkyl group, C₄˜C₃₀ hetero aryl amino groupunsubstituted or substituted with linear or branched C₁˜C₁₀ alkyl group,C₅˜C₃₀ aryl group unsubstituted or substituted with a group selectedfrom the group consisting of linear or branched C₁˜C₁₀ alkyl group,C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero aryl group and combination thereof; orC₄˜C₃₀ hetero aryl group unsubstituted or substituted with a groupselected from the group consisting of linear or branched C₁˜C₁₀ alkylgroup, C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero aryl group and combinationthereof; each of o and p is independently a number of substituents, R₁₃and R₁₄ and an integer of 1 to 2; and each of m and n is identical asdefined in Chemical Formula
 1. 7. The light emitting diode of claim 5,wherein the organic compound has the following structure of ChemicalFormula 3:

wherein each of R₂₁ and R₂₂ is independently protium, deuterium,tritium, linear or branched C₁˜C₁₀ alkyl group or C₁˜C₁₀ alkoxy group;each of R₂₃ to R₂₆ is independently C₅˜C₃₀ aryl group unsubstituted orsubstituted with a group selected from the group consisting of linear orbranched C₁˜C₁₀ alkyl group, C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero aryl groupand combination thereof; or C₄˜C₃₀ hetero aryl group unsubstituted orsubstituted with a group selected from the group consisting of linear orbranched C₁˜C₁₀ alkyl group, C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero aryl groupand combination thereof, and each of m and n is identical as defined inChemical Formula
 1. 8. The light emitting diode of claim 5, wherein theorganic compound includes anyone having the following structure ofChemical Formula
 4.


9. The light emitting diode of claim 5, wherein the emissive layerfurther comprises an emitting material layer.
 10. The light emittingdiode of claim 9, wherein the hole transfer layer is disposed betweenthe emitting material layer and one of the first and second electrodesacting as an anode.
 11. The light emitting diode of claim 10, whereinthe hole transfer layer includes a hole injection layer between theanode and the emitting material layer and a hole transport layerdisposed between the hole injection layer and the emitting materiallayer.
 12. The light emitting diode of claim 11, wherein the holetransport layer includes the organic compound.
 13. The light emittingdiode of claim 12, wherein the hole transport layer includes the organiccompound as a dopant.
 14. The light emitting diode of claim 13, whereinthe hole transport layer include anyone host having the followingstructure of Chemical Formulae 5 to 8:

wherein each of R₃₁ to R₃₄ is independently unsubstituted or substitutedlinear or branched C₁˜C₂₀ alkyl group, unsubstituted or substitutedC₁˜C₂₀ alkoxy group, unsubstituted or substituted C₅˜C₃₀ aryl group orunsubstituted or substituted C₄˜C₃₀ hetero aryl group; each of a and bis independently an integer of 1 to 4; n is an integer of equal to ormore than 1; and m is an integer of 1 to
 10. 15. The light emittingdiode of claim 11, wherein the hole transport layer includes a firsthole transport layer disposed between the hole injection layer and theemitting material layer and a second hole transport layer disposedbetween the first hole transport layer and the emitting material layer.16. The light emitting diode of claim 15, wherein the second holetransport layer includes the organic compound.
 17. The light emittingdiode of claim 15, wherein the first hole transport layer includes anorganic material having anyone of the following structure of ChemicalFormulae 5 to 8:

wherein each of R₃₁ to R₃₄ is independently unsubstituted or substitutedlinear or branched C₁˜C₂₀ alkyl group, unsubstituted or substitutedC₁˜C₂₀ alkoxy group, unsubstituted or substituted C₅˜C₃₀ aryl group orunsubstituted or substituted C₄˜C₃₀ hetero aryl group; each of a and bis independently an integer of 1 to 4; n is an integer of equal to ormore than 1; and m is an integer of 1 to
 10. 18. The light emittingdiode of claim 9, wherein the emitting material layer includes inorganicluminescent particles.
 19. The light emitting diode of claim 18, whereinthe inorganic luminescent particles include quantum dots (QDs) orquantum rods (QRs).
 20. A light emitting device, comprising: asubstrate; and a light emitting diode according to claim 5 over thesubstrate.
 21. The light emitting device of claim 20, wherein theorganic compound includes an organic compound having the followingstructure of Chemical Formula 2:

wherein each of R₁₁ and R₁₂ is independently protium, deuterium,tritium, linear or branched C₁˜C₁₀ alkyl group or C₁˜C₁₀ alkoxy group;each of Ar_(a) and Ar₄ is independently C₁₀˜C₃₀ fused hetero aryl group;each of R₁₃ and R₁₄ is independently linear or branched C₁˜C₁₀ alkylgroup, C₅˜C₃₀ aryl amino group unsubstituted or substituted with linearor branched C₁˜C₁₀ alkyl group, C₄˜C₃₀ hetero aryl amino groupunsubstituted or substituted with linear or branched C₁˜C₁₀ alkyl group,C₅˜C₃₀ aryl group unsubstituted or substituted with a group selectedfrom the group consisting of linear or branched C₁˜C₁₀ alkyl group,C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero aryl group and combination thereof; orC₄˜C₃₀ hetero aryl group unsubstituted or substituted with a groupselected from the group consisting of linear or branched C₁˜C₁₀ alkylgroup, C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero aryl group and combinationthereof, each of o and p is independently a number of substituent, R₁₃and R₁₄ and an integer of 1 to 2; and each of m and n is identical asdefined in Chemical Formula
 1. 22. The light emitting device of claim20, wherein the organic compound includes an organic compound having thefollowing structure of Chemical Formula 3:

wherein each of R₂₁ and R₂₂ is independently protium, deuterium,tritium, linear or branched C₁˜C₁₀ alkyl group or C₁˜C₁₀ alkoxy group;each of R₂₃ to R₂₆ is independently C₅˜C₃₀ aryl group unsubstituted orsubstituted with a group selected from the group consisting of linear orbranched C₁˜C₁₀ alkyl group, C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero aryl groupand combination thereof; or C₄˜C₃₀ hetero aryl group unsubstituted orsubstituted with a group selected from the group consisting of linear orbranched C₁˜C₁₀ alkyl group, C₅˜C₃₀ aryl group, C₄˜C₃₀ hetero aryl groupand combination thereof, and each of m and n is identical as defined inChemical Formula
 1. 23. The light emitting device of claim 20, whereinthe light emitting device includes a light emitting display device and alight emitting illumination device.